KR19990007873A - Dihalopropene compounds, pesticides containing them as active ingredients, and intermediates for their preparation - Google Patents

Dihalopropene compounds, pesticides containing them as active ingredients, and intermediates for their preparation Download PDF

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Publication number
KR19990007873A
KR19990007873A KR1019970707396A KR19970707396A KR19990007873A KR 19990007873 A KR19990007873 A KR 19990007873A KR 1019970707396 A KR1019970707396 A KR 1019970707396A KR 19970707396 A KR19970707396 A KR 19970707396A KR 19990007873 A KR19990007873 A KR 19990007873A
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South Korea
Prior art keywords
dichloro
phenol
alkyl
propenyloxy
pyridyl
Prior art date
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KR1019970707396A
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Korean (ko)
Inventor
산시로 마쓰오
다로 히로세
게이이찌 이즈미
마사야 스즈끼
노리야스 사까모또
가즈노리 쓰시마
시게루 사이또
히로따까 다까노
Original Assignee
고사이 아끼오
스미또모 가가꾸 고오교 가부시끼가이샤
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Application filed by 고사이 아끼오, 스미또모 가가꾸 고오교 가부시끼가이샤 filed Critical 고사이 아끼오
Publication of KR19990007873A publication Critical patent/KR19990007873A/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
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Abstract

본 발명의 목적은 우수한 살충 활성을 가지고 있어서 해충 억제에 만족스러울만큼 효과적인 하기 화학식 (1)의 디할로프로펜 화합물을 제공하는 것이다:It is an object of the present invention to provide a dihalopropene compound of formula (1) having good pesticidal activity and which is satisfactorily effective in inhibiting pests:

[화학식 1][Formula 1]

[식 중, R1은 C1-C10알킬 등이고;[Wherein, R 1 is C 1 -C 10 alkyl or the like;

L은 C(=O)NH 등이고;L is C (= 0) NH or the like;

R2, R3및 R4는 독립적으로 할로겐 등이며;R 2 , R 3 and R 4 are independently halogen or the like;

R5, R6및 R7은 독립적으로 수소 등이고;R 5 , R 6 and R 7 are independently hydrogen or the like;

m은 0 내지 4의 정수이고;m is an integer from 0 to 4;

n은 0 내지 2의 정수이고;n is an integer from 0 to 2;

X는 염소 등이고;X is chlorine or the like;

Y는 산소 등이고;Y is oxygen or the like;

Z는 산소 등이다].Z is oxygen or the like].

Description

디할로프로펜 화합물, 이를 활성 성분으로 함유하는 살충제, 및 그의 제조를 위한 중간체Dihalopropene compounds, pesticides containing them as active ingredients, and intermediates for their preparation

예컨대 JP-A-48-86835/1974호 및 JP-A-49-1526/1974호에 기술된 대로, 몇몇 종류의 프로펜 화합물이 살충제의 활성 성분으로서 사용될 수 있음이 공지되어 있다.It is known that several kinds of propene compounds can be used as active ingredients of pesticides, as described, for example, in JP-A-48-86835 / 1974 and JP-A-49-1526 / 1974.

그러나 살충 활성의 관점에서, 상기 화합물이 해충을 억제하는데 늘 만족스러울만큼 효과적이라고는 말할 수 없다.However, in terms of pesticidal activity, it cannot be said that the compounds are always satisfactorily effective in inhibiting pests.

발명의 개시Disclosure of the Invention

본 발명자들은 열띤 연구 끝에 뛰어난 살충 활성을 갖는 화합물을 발견하였다. 그리하여 그들은 특정한 디할로프로펜 화합물이 해충의 억제에 만족스러울만큼 살충 활성을 가지는 것을 발견하였다.The inventors have found compounds with excellent pesticidal activity after intense studies. Thus, they found that certain dihalopropene compounds had pesticidal activity that was satisfactory for the inhibition of pests.

즉, 본 발명의 목적은 하기 화학식(1)의 디할로프로펜 화합물을 제공하는 것이다:That is, an object of the present invention is to provide a dihalopropene compound of formula (1):

[화학식 1][Formula 1]

[식중, m은 0 내지 4의 정수이고; n은 0 내지 2의 정수이며; X는 독립적으로 염소 또는 브롬이고; Y는 산소, NH 또는 황이며; Z는 산소, 황 또는 NR15(식중, R15는 수소 또는 C1-C3알킬이다)이고; R2, R3및 R4는 독립적으로 할로겐, C1-C3할로알킬 또는 C1-C3알킬이며; R5, R6및 R7은 독립적으로 수소, C1-C3알킬 또는 트리플루오로메틸이고; L은 C=W, C(=W)NR13, NR13C(=W), SO2NR13, NR13SO2, NR13C(=W1)W, WC(=W1)NR13또는 NR14C(=W)NR13(식중, W 및 W1은 독립적으로 산소 또는 황이고, R13및 R14는 독립적으로 수소, C1-C10알킬, C1-C5할로알킬, C2-C10알케닐, C2-C6할로알케닐, C3-C9알키닐 또는 C3-C5할로알키닐이다)이고; R1은 C1-C10알킬, C1-C5할로알킬, C2-C10알케닐, C2-C6할로알케닐, C3-C9알키닐, C3-C5할로알키닐, C2-C7알콕시알킬, C2-C7알킬티오알킬, C1-C4알킬, C1-C4알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 C3-C6시클로알킬, C1-C4알킬로 치환될 수도 있는 C4-C9시클로알킬알킬, C1-C4알킬로 치환될 수도 있는 C5-C6시클로알케닐, C1-C4알킬로 치환될 수도 있는 C6-C8시클로알케닐알킬, 또는 하기 화학식 Q1, Q2, Q3또는 Q4의, 치환될 수도 있는 복소환 기:[Wherein m is an integer of 0 to 4; n is an integer from 0 to 2; X is independently chlorine or bromine; Y is oxygen, NH or sulfur; Z is oxygen, sulfur or NR 15 , wherein R 15 is hydrogen or C 1 -C 3 alkyl; R 2 , R 3 and R 4 are independently halogen, C 1 -C 3 haloalkyl or C 1 -C 3 alkyl; R 5 , R 6 and R 7 are independently hydrogen, C 1 -C 3 alkyl or trifluoromethyl; L is C = W, C (= W) NR 13 , NR 13 C (= W), SO 2 NR 13 , NR 13 SO 2 , NR 13 C (= W 1 ) W, WC (= W 1 ) NR 13 Or NR 14 C (═W) NR 13 wherein W and W 1 are independently oxygen or sulfur, R 13 and R 14 are independently hydrogen, C 1 -C 10 alkyl, C 1 -C 5 haloalkyl, C 2 -C 10 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 9 alkynyl or C 3 -C 5 haloalkynyl); R 1 is C 1 -C 10 alkyl, C 1 -C 5 haloalkyl, C 2 -C 10 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 9 alkynyl, C 3 -C 5 haloalky C 3 -C 6, which may be substituted by Nyl, C 2 -C 7 alkoxyalkyl, C 2 -C 7 alkylthioalkyl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 1 -C 3 haloalkoxy a cycloalkyl, C 1 -C 4 alkyl, optionally substituted C 4 -C 9 cycloalkyl alkyl, C 1 -C 4 optionally substituted C 5 -C 6 cycloalkenyl, C 1 -C 4 alkyl with alkyl as C 6 -C 8 cycloalkenylalkyl which may be substituted, or a heterocyclic group which may be substituted, of the general formula Q 1 , Q 2 , Q 3 or Q 4 :

[화학식 2][Formula 2]

[식중, M은 산소, NH 또는 황이고, l은 0 내지 5의 정수이고, p는 0 내지 5의 정수이고, q는 1 내지 5의 정수이며; R12는 할로겐, 시아노, 니트로, 펜타플루오로술파닐(F5S), C1-C8알킬, C1-C3할로알킬, C1-C7알콕시, C1-C3할로알콕시, C1-C3알킬티오, C1-C3할로알킬티오, C3-C6알케닐옥시, C3-C6할로알케닐옥시, C1-C3히드록시알킬, C2-C4알케닐, C2-C4할로알케닐, C2-C4알키닐, C2-C4알키닐옥시, C2-C4할로알키닐, C2-C4할로알키닐옥시, C2-C4알콕시알킬, C2-C4알킬티오알킬, C3-C6시클로알킬, C5-C6시클로알케닐, C2-C5알콕시카르보닐, C3-C6시클로알킬옥시, C5-C6시클로알케닐옥시, 할로겐, C1-C4알킬, C1-C3할로알킬, C1-C3알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 페닐, 할로겐, C1-C4알킬, C1-C3할로알킬, C1-C3알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 페녹시, 할로겐, C1-C4알킬, C1-C3할로알킬, C1-C3알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 벤질, 할로겐, C1-C4알킬, C1-C3할로알킬, C1-C3알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 벤질옥시이거나; 또는 l이 2 내지 5의 정수일 때, 인접한 두 R12는 그들의 말단부에서 함께 결합하여 트리메틸렌이나 테트라메틸렌, 할로겐이나 C1-C3알킬로 치환될 수도 있는 메틸렌디옥시, 또는 할로겐이나 C1-C3알킬로 치환될 수도 있는 에틸렌디옥시를 형성하며; 그리고 R8, R9, R10및 R11은 독립적으로 수소, C1-C3알킬 또는 트리플루오로메틸이다].[Wherein M is oxygen, NH or sulfur, l is an integer of 0 to 5, p is an integer of 0 to 5, q is an integer of 1 to 5; R 12 is halogen, cyano, nitro, pentafluorosulfanyl (F 5 S), C 1 -C 8 alkyl, C 1 -C 3 haloalkyl, C 1 -C 7 alkoxy, C 1 -C 3 haloalkoxy , C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, C 3 -C 6 alkenyloxy, C 3 -C 6 haloalkenyloxy, C 1 -C 3 hydroxyalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 alkynyloxy, C 2 -C 4 haloalkynyl, C 2 -C 4 haloalkynyloxy, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkylthioalkyl, C 3 -C 6 cycloalkyl, C 5 -C 6 cycloalkenyl, C 2 -C 5 alkoxycarbonyl, C 3 -C 6 cycloalkyloxy Phenyl, halogen which may be substituted by C 5 -C 6 cycloalkenyloxy, halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy Phenoxy, halogen, C 1 -C 4 alkyl, C 1 -which may be substituted by C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy C 3 haloalkyl, C 1 -C 3 Which may be substituted with koksi or C 1 -C 3 haloalkoxy, benzyl, halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy substituted with May be benzyloxy; Or when l is an integer from 2 to 5, two adjacent R 12 's are bonded together at their termini to methylenedioxy, which may be substituted with trimethylene or tetramethylene, halogen or C 1 -C 3 alkyl, or halogen or C 1- Forms ethylenedioxy, which may be substituted with C 3 alkyl; And R 8 , R 9 , R 10 and R 11 are independently hydrogen, C 1 -C 3 alkyl or trifluoromethyl].

또한 본 발명의 목적은 본 발명에 의한 화합물중의 일부의 제조를 위한 중간체로서 유용한 하기 화학식(3)의 화합물을 제공하는 것이다.It is also an object of the present invention to provide compounds of formula (3) which are useful as intermediates for the preparation of some of the compounds according to the invention.

[화학식 3][Formula 3]

[식중, X는 독립적으로 염소 또는 브롬이고; R18및 R19는 독립적으로 할로겐 또는 C1-C3알킬이며; R17은 아미노 또는 카르복실이고; R5, R6및 R7은 독립적으로 수소, C1-C3알킬 또는 트리플루오로메틸이며; m은 0 내지 4의 정수이다].[Wherein X is independently chlorine or bromine; R 18 and R 19 are independently halogen or C 1 -C 3 alkyl; R 17 is amino or carboxyl; R 5 , R 6 and R 7 are independently hydrogen, C 1 -C 3 alkyl or trifluoromethyl; m is an integer from 0 to 4;

좀 더 구체적으로, 본 발명의 목적은 하기 화학식(4)의 페놀 화합물을 제공하는 것이다.More specifically, it is an object of the present invention to provide a phenolic compound of formula (4).

[화학식 4][Formula 4]

[식중, R20은 상기 정의된 Q1이거나, 각각 (R16)s(식중, R16은 할로겐, 니트로, 시아노, C1-C4알킬, C1-C3할로알킬, C1-C4알콕시, C1-C3할로알콕시, C1-C3알킬티오, C1-C3할로알킬티오, C1-C2알킬술피닐, C1-C2알킬술포닐, C1-C2할로알킬술피닐, C1-C2할로알킬술포닐, C2-C4알케닐, C2-C4할로알케닐, C2-C4알키닐, C2-C4할로알키닐, 아미노, 디메틸아미노, 아세트아미도, 아세틸, 할로아세틸, 포르밀, 카르복실, 메톡시카르보닐, C3-C6시클로알킬, (C1-C2알킬)아미노카르보닐, [디(C1-C2알킬)아미노]카르보닐, 할로겐, C1-C4알킬, C1-C3할로알킬, C1-C4알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 페닐, 할로겐, C1-C4알킬, C1-C3할로알킬, C1-C4알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 벤질, 할로겐, C1-C4알킬, C1-C3할로알킬, C1-C4알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 페녹시, 할로겐, C1-C4알킬, C1-C3할로알킬, C1-C4알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 벤질옥시, 또는 할로겐, C1-C4알킬, C1-C3할로알킬, C1-C4알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 피리딜옥시이고; s는 0 내지 7의 정수이다)으로 치환될 수도 있는 2-피리딜, 2-피라지닐, 2-인돌릴, 2-피롤릴, 2-퀴놀릴, 2-티에닐, 3-티에닐, 2-푸릴, 3-푸릴, 3-피리딜 또는 4-피리딜이며; R2및 R3는 독립적으로 할로겐, C1-C3할로알킬 또는 C1-C3알킬이고; R5, R6및 R7은 독립적으로 수소, C1-C3알킬 또는 트리플루오로메틸이며; L1은 C=W, C(=W)NR131또는 SO2NR131(식중, W는 산소 또는 황이고, R131은 수소 또는 C1-C3알킬이다)이다][Wherein R 20 is Q 1 as defined above or each of (R 16 ) s (wherein R 16 is halogen, nitro, cyano, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1- C 4 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, C 1 -C 2 alkylsulfinyl, C 1 -C 2 alkylsulfonyl, C 1- C 2 haloalkylsulfinyl, C 1 -C 2 haloalkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl , Amino, dimethylamino, acetamido, acetyl, haloacetyl, formyl, carboxyl, methoxycarbonyl, C 3 -C 6 cycloalkyl, (C 1 -C 2 alkyl) aminocarbonyl, [di (C Phenyl, halogen which may be substituted by 1- C 2 alkyl) amino] carbonyl, halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 3 haloalkoxy , C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 3 haloalkyl optionally substituted benzyl as alkoxy, halogen, C 1 -C 4 al , C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 3 haloalkyl during alkoxy which may be substituted by phenoxy, halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 Benzyloxy, or halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 3 , which may be substituted with -C 4 alkoxy or C 1 -C 3 haloalkoxy Pyridyloxy, which may be substituted with haloalkoxy; s is an integer from 0 to 7), 2-pyridyl, 2-pyrazinyl, 2-indolyl, 2-pyrrolyl, 2-quinolyl , 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 3-pyridyl or 4-pyridyl; R 2 and R 3 are independently halogen, C 1 -C 3 haloalkyl or C 1 -C 3 alkyl; R 5 , R 6 and R 7 are independently hydrogen, C 1 -C 3 alkyl or trifluoromethyl; L 1 is C = W, C (= W) NR 131 or SO 2 NR 131 (wherein W is oxygen or sulfur and R 131 is hydrogen or C 1 -C 3 alkyl)

상기 페놀 화합물의 좀 더 특정한 예로서, 본 발명의 목적은 R20이 Q1(식중, p=0이다) 또는 상기 정의된 R1(식중, 5- 또는 6-원 복소환 기가 2-피라지닐, 2-인돌릴, 2-피롤릴, 2-퀴롤릴, 2-티에닐, 3-티에닐, 2-푸릴, 3-푸릴, 2-피리딜, 3-피리딜 또는 4-피리딜이다)인 페놀 화합물; R20이 Q1(식중, p=0이다) 또는 상기 정의된 R1(식중, 5- 또는 6-원 복소환 기가 2-피라지닐, 2-인돌릴, 2-피롤릴, 2-퀴놀릴, 2-티에닐, 3-티에닐, 2-푸릴, 3-푸릴, 2-피리딜, 3-피리딜 또는 4-피리딜이다)이고; L1은 C(=W)NR131또는 SO2NR131인 페놀 화합물; R20이 Q1(식중, p=0이다) 또는 상기 정의된 R1(식중, 5- 또는 6-원 복소환 기가 2-피라지닐, 2-인돌릴, 2-피롤릴, 2-퀴놀릴, 2-티에닐, 3-티에닐, 2-푸릴, 3-푸릴, 2-피리딜, 3-피리딜 또는 4-피리딜이다) 이고; R2및 R3은 할로겐 또는 C1-C3알킬이고; L1은 C(=W)NR131또는 SO2NR131인 페놀 화합물; 및 하기의 화합물을 제공하는 것이다:As a more specific example of the phenolic compound, it is an object of the present invention that R 20 is Q 1 (where p = 0) or R 1 as defined above, wherein the 5- or 6-membered heterocyclic group is 2-pyrazinyl , 2-indolyl, 2-pyrrolyl, 2-quirrolyl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-pyridyl, 3-pyridyl or 4-pyridyl) Phosphorus phenol compounds; R 20 is Q 1 (where p = 0) or R 1 as defined above wherein the 5- or 6-membered heterocyclic group is 2-pyrazinyl, 2-indolyl, 2-pyrrolyl, 2-quinolyl , 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-pyridyl, 3-pyridyl or 4-pyridyl); L 1 is a phenolic compound of C (= W) NR 131 or SO 2 NR 131 ; R 20 is Q 1 (where p = 0) or R 1 as defined above wherein the 5- or 6-membered heterocyclic group is 2-pyrazinyl, 2-indolyl, 2-pyrrolyl, 2-quinolyl , 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-pyridyl, 3-pyridyl or 4-pyridyl); R 2 and R 3 are halogen or C 1 -C 3 alkyl; L 1 is a phenolic compound of C (= W) NR 131 or SO 2 NR 131 ; And to provide the following compounds:

3,5-디클로로-4-(3-(N-(4-트리플루오로메틸페닐)카르바모일)프로필옥시)-페놀;3,5-dichloro-4- (3- (N- (4-trifluoromethylphenyl) carbamoyl) propyloxy) -phenol;

3,5-디클로로-4-(4-(N-(4-트리플루오로메틸페닐)카르바모일)부틸옥시)-페놀;3,5-dichloro-4- (4- (N- (4-trifluoromethylphenyl) carbamoyl) butyloxy) -phenol;

3,5-디클로로-4-(3-(N-(5-트리플루오로메틸-2-피리딜)카르바모일)프로필옥시)-페놀;3,5-dichloro-4- (3- (N- (5-trifluoromethyl-2-pyridyl) carbamoyl) propyloxy) -phenol;

3,5-디클로로-4-(4-(N-(5-트리플루오로메틸-2-피리딜)카르바모일)부틸옥시)-페놀.3,5-dichloro-4- (4- (N- (5-trifluoromethyl-2-pyridyl) carbamoyl) butyloxy) -phenol.

본 발명은 디할로프로펜 화합물, 이를 활성 성분으로 함유하는 살충제, 및 그의 제조를 위한 중간체에 관한 것이다.The present invention relates to dihalopropene compounds, pesticides containing them as active ingredients, and intermediates for their preparation.

본 발명에 의한 화합물 및 그의 중간체에 대한 상기 식에서의 변수는 하기의 특정한 예에서 취할 수 있다.The variables in the above formulas for the compounds according to the invention and their intermediates can be taken in the following specific examples.

R1에서 표현된, 치환될 수도 있는 복소환 기 상의 치환기의 예로는 하기식의 치환기가 있다:Examples of substituents on the optionally substituted heterocyclic group represented by R 1 are substituents of the following formula:

(R16)s[식중, R16은 할로겐, 니트로, 시아노, C1-C4알킬, C1-C3할로알킬, C1-C4알콕시, C1-C3할로알콕시, C1-C3알킬티오, C1-C3할로알킬티오, C1-C2알킬술피닐, C1-C2알킬술포닐, C1-C2할로알킬술피닐, C1-C2할로알킬술포닐, C2-C4알케닐, C2-C4할로알케닐, C2-C4알키닐, C2-C4할로알키닐, 아미노, 디메틸아미노, 아세트아미도, 아세틸, 할로아세틸, 포르밀, 카르복실, 메톡시카르보닐, C3-C6시클로알킬, (C1-C2알킬)아미노카르보닐, [디(C1-C2알킬)아미노]카르보닐, 할로겐, C1-C4알킬, C1-C3할로알킬, C1-C4알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 페닐, 할로겐, C1-C4알킬, C1-C3할로알킬, C1-C4알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 벤질, 할로겐, C1-C4알킬, C1-C3할로알킬, C1-C4알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 페녹시, 할로겐, C1-C4알킬, C1-C3할로알킬, C1-C4알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 벤질옥시, 또는 할로겐, C1-C4알킬, C1-C3할로알킬, C1-C4알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 피리딜옥시이고; s는 0 내지 7의 정수이다].(R 16 ) s where R 16 is halogen, nitro, cyano, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, C 1 -C 2 alkylsulfinyl, C 1 -C 2 alkylsulfonyl, C 1 -C 2 haloalkylsulfinyl, C 1 -C 2 haloalkyl, Sulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, amino, dimethylamino, acetamido, acetyl, haloacetyl , Formyl, carboxyl, methoxycarbonyl, C 3 -C 6 cycloalkyl, (C 1 -C 2 alkyl) aminocarbonyl, [di (C 1 -C 2 alkyl) amino] carbonyl, halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 3 haloalkoxy, optionally substituted phenyl, halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl Benzyl, halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy or C 1 which may be substituted by alkyl, C 1 -C 4 alkoxy or C 1 -C 3 haloalkoxy -C 3 haloalkyl during which may be substituted with a phenoxy alkoxy, halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy or C 1 -C benzyl which may be substituted with 3 haloalkoxy Oxy or pyridyloxy which may be substituted by halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 3 haloalkoxy; s is an integer of 0 to 7].

R2, R3, R4, R12, R16, R18또는 R19에 표현된, 혹은 R12또는 R16에 존재하는 할로겐의 예로는 불소, 염소, 브롬 및 요오드가 있다.Examples of halogen represented by R 2 , R 3 , R 4 , R 12 , R 16 , R 18 or R 19 , or present in R 12 or R 16 are fluorine, chlorine, bromine and iodine.

R1, R13또는 R14에 표현된 C1-C10알킬기의 예로는 메틸, 에틸, n-프로필, 이소프로필, n-부틸, 이소부틸, sec-부틸, tert-부틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, n-헥실, n-헵틸, 이소헥실, n-옥틸, n-노닐, n-데실, 1-에틸프로필, 2-에틸부틸, 1-메틸펜틸, 1-에틸부틸, 3-메틸펜틸, 1,3-디메틸부틸, 1-메틸헵틸 및 1-메틸옥틸이 있다.Examples of C 1 -C 10 alkyl groups represented by R 1 , R 13 or R 14 are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, Isopentyl, neopentyl, tert-pentyl, n-hexyl, n-heptyl, isohexyl, n-octyl, n-nonyl, n-decyl, 1-ethylpropyl, 2-ethylbutyl, 1-methylpentyl, 1- Ethylbutyl, 3-methylpentyl, 1,3-dimethylbutyl, 1-methylheptyl and 1-methyloctyl.

R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R15, R18또는 R19에 표현된 C1-C3알킬기의 예로는 메틸, 에틸, n-프로필 및 이소프로필이 있다.Examples of C 1 -C 3 alkyl groups represented by R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 15 , R 18 or R 19 include Methyl, ethyl, n-propyl and isopropyl.

R12에 표현된 C1-C8알킬기의 예로는 메틸, 에틸, n-프로필, 이소프로필, n-부틸, 이소부틸, sec-부틸, tert-부틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 1-에틸펜틸, n-헥실, 이소헥실, 2-에틸부틸, 1-메틸펜틸, 1-에틸부틸, 3-메틸펜틸, 1,3-디메틸부틸, n-헵틸, n-옥틸 및 1-메틸헵틸이 있다.Examples of C 1 -C 8 alkyl group represented by R 12 include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethylpentyl, n-hexyl, isohexyl, 2-ethylbutyl, 1-methylpentyl, 1-ethylbutyl, 3-methylpentyl, 1,3-dimethylbutyl, n-heptyl, n-octyl And 1-methylheptyl.

R16에 존재하는 C1-C2알킬기의 예로는 메틸과 에틸이 있다.Examples of C 1 -C 2 alkyl groups present in R 16 are methyl and ethyl.

R1, R13또는 R14에 표현된 C1-C5할로알킬기의 예로는 트리플루오로메틸, 디플루오로메틸, 브로모디플루오로메틸, 2,2,2-트리플루오로에틸, 퍼플루오로에틸, 2-플루오로에틸, 2-클로로에틸, 2-브로모에틸, 2-요오도에틸, 2,2-디클로로에틸, 2-브로모-1,1,2,2-테트라플루오로에틸, 1,1,2,2-테트라플루오로에틸, 2-클로로-1,1,2-트리플루오로에틸, 2-브로모-1,1,2-트리플루오로에틸, 2,2,2-트리클로로에틸, 2,2,2-트리브로모에틸, 3-클로로프로필, 3-브로모프로필, 3-플루오로프로필, 3-요오도프로필, 3,3,3-트리플루오로프로필, 2,2,3,3,3-펜타플루오로프로필, 1,1,2,3,3,3-헥사플루오로프로필, 2-클로로프로필, 1-클로로-1-메틸에틸, 1-브로모-1-메틸에틸, 2-플루오로-1-(플루오로메틸)에틸, 2-클로로-1-(클로로메틸)에틸, 2-브로모-1-(브로모메틸)에틸, 2,2,2-트리플루오로-1-(트리플루오로메틸)에틸, 2,3-디브로모프로필, 4-플루오로부틸, 4-브로모부틸, 4-클로로부틸, 4-요오도부틸, 2-(브로모메틸)프로필, 3-클로로-2,2-디메틸-n-프로필, 3-브로모-2,2-디메틸프로필, 2,2,3,4,4,4-헥사플루오로부틸, 3-브로모-(1-브르모메틸)프로필 및 2,2,3,3,4,4,5,5-옥타플루오로펜틸이 있다.Examples of C 1 -C 5 haloalkyl groups represented by R 1 , R 13 or R 14 are trifluoromethyl, difluoromethyl, bromodifluoromethyl, 2,2,2-trifluoroethyl, perfluoro Roethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-dichloroethyl, 2-bromo-1,1,2,2-tetrafluoroethyl , 1,1,2,2-tetrafluoroethyl, 2-chloro-1,1,2-trifluoroethyl, 2-bromo-1,1,2-trifluoroethyl, 2,2,2 Trichloroethyl, 2,2,2-tribromoethyl, 3-chloropropyl, 3-bromopropyl, 3-fluoropropyl, 3-iodopropyl, 3,3,3-trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, 1,1,2,3,3,3-hexafluoropropyl, 2-chloropropyl, 1-chloro-1-methylethyl, 1-bromo -1-methylethyl, 2-fluoro-1- (fluoromethyl) ethyl, 2-chloro-1- (chloromethyl) ethyl, 2-bromo-1- (bromomethyl) ethyl, 2,2, 2-trifluoro-1- (trifluoro Ethyl), 2,3-dibromopropyl, 4-fluorobutyl, 4-bromobutyl, 4-chlorobutyl, 4-iodobutyl, 2- (bromomethyl) propyl, 3-chloro-2 , 2-dimethyl-n-propyl, 3-bromo-2,2-dimethylpropyl, 2,2,3,4,4,4-hexafluorobutyl, 3-bromo- (1-bromomethyl) Propyl and 2,2,3,3,4,4,5,5-octafluoropentyl.

R2, R3, R4, R12또는 R16에 표현된, 혹은 R12또는 R16에 존재하는 C1-C3할로알킬기의 예로는 트리플루오로메틸, 디플루오로메틸, 브로모디플루오로메틸, 2,2,2-트리플루오로에틸, 2-플루오로에틸, 2-클로로에틸, 2-브로모에틸, 1-플루오로에틸, 1-클로로에틸, 1-브로모에틸, 2,2,3,3,3-펜타플루오로프로필, 3,3,3-트리플루오로프로필, 1-플루오로프로필, 2-클로로프로필 및 3-브로모프로필이 있다.Examples of C 1 -C 3 haloalkyl groups represented by R 2 , R 3 , R 4 , R 12 or R 16 , or present in R 12 or R 16 are trifluoromethyl, difluoromethyl, bromodifluoro Chloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 1-fluoroethyl, 1-chloroethyl, 1-bromoethyl, 2, 2,3,3,3-pentafluoropropyl, 3,3,3-trifluoropropyl, 1-fluoropropyl, 2-chloropropyl and 3-bromopropyl.

R1, R13또는 R14에 표현된 C2-C10알케닐기의 예로는 비닐, 알릴, 호모알릴, 이소프로페닐, 2-부테닐, 1-메틸-2-프로페닐, 프레닐, 3-메틸-3-부테닐, 1-에틸-2-프로페닐, 2-에틸-2-프로페닐, 2-펜테닐, 2-메틸-2-부테닐, 1-메틸-2-부테닐, 2-메틸-3-부테닐, 4-펜테닐, 1-메틸-3-부테닐, 1-에틸-2-프로페닐, 1-프로필-2-프로페닐, 3-헥세닐, 2-이소프로필-2-프로페닐, 2-에틸-2-부테닐, 2-메틸-2-펜테닐, 1-에틸-2-부테닐, 1-메틸-4-펜테닐, 1,3-디메틸-2-부테닐, 2-헥세닐, 4-헥세닐, 5-헥세닐, 1-n-프로필-2-프로페닐, 1-알릴-3-부테닐, 2-헵테닐, 1,5-디메틸-4-헥세닐, 1-펜틸-2-프로페닐, 1,7-디메틸-6-옥테닐 및 제라닐이 있다.Examples of C 2 -C 10 alkenyl groups represented by R 1 , R 13 or R 14 include vinyl, allyl, homoallyl, isopropenyl, 2-butenyl, 1-methyl-2-propenyl, prenyl, 3 -Methyl-3-butenyl, 1-ethyl-2-propenyl, 2-ethyl-2-propenyl, 2-pentenyl, 2-methyl-2-butenyl, 1-methyl-2-butenyl, 2 -Methyl-3-butenyl, 4-pentenyl, 1-methyl-3-butenyl, 1-ethyl-2-propenyl, 1-propyl-2-propenyl, 3-hexenyl, 2-isopropyl- 2-propenyl, 2-ethyl-2-butenyl, 2-methyl-2-pentenyl, 1-ethyl-2-butenyl, 1-methyl-4-pentenyl, 1,3-dimethyl-2-part Tenyl, 2-hexenyl, 4-hexenyl, 5-hexenyl, 1-n-propyl-2-propenyl, 1-allyl-3-butenyl, 2-heptenyl, 1,5-dimethyl-4- Hexenyl, 1-pentyl-2-propenyl, 1,7-dimethyl-6-octenyl and geranyl.

R1, R13또는 R14에 표현된 C2-C10할로알케닐기의 예로는 2-클로로에테닐, 2,2-디클로로에테닐, 3-클로로-2-프로페닐, 3-브로모-2-프로페닐, 2-클로로-2-프로페닐, 2-브로모-2-프로페닐, 3,3-디클로로-2-프로페닐, 3,3-디브로모-2-프로페닐, 3,3-디플루오로-2-프로페닐, 2-클로로메틸-2-프로페닐, 4-클로로-2-부테닐, 4-클로로-2-부테닐, 3-클로로-4,4,4-트리플루오로-2-부테닐, 4-브로모-3-플루오로-4,4-디플루오로-2-부테닐, 3,4,4,4-테트라플루오로-2-부테닐, 4,4-디클로로-3-부테닐, 4,4-디브로모-3-부테닐, 4,4,4-트리플루오로-3-부테닐, 3-클로로-2-부테닐 및 6,6-디클로로-5-헥세닐이 있다.Examples of C 2 -C 10 haloalkenyl groups represented by R 1 , R 13 or R 14 are 2-chloroethenyl, 2,2-dichloroethenyl, 3-chloro-2-propenyl, 3-bromo- 2-propenyl, 2-chloro-2-propenyl, 2-bromo-2-propenyl, 3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl, 3, 3-difluoro-2-propenyl, 2-chloromethyl-2-propenyl, 4-chloro-2-butenyl, 4-chloro-2-butenyl, 3-chloro-4,4,4-tri Fluoro-2-butenyl, 4-bromo-3-fluoro-4,4-difluoro-2-butenyl, 3,4,4,4-tetrafluoro-2-butenyl, 4, 4-dichloro-3-butenyl, 4,4-dibromo-3-butenyl, 4,4,4-trifluoro-3-butenyl, 3-chloro-2-butenyl and 6,6- Dichloro-5-hexenyl.

R12또는 R16에 표현된 C2-C4알케닐기의 예로는 비닐, 이소프로페닐, 1-프로페닐, 2-에틸-1-프로페닐, 1-메틸-1-프로페닐, 알릴, 2-메틸프로페닐 및 2-부테닐이 있다.Examples of the C 2 -C 4 alkenyl group represented by R 12 or R 16 include vinyl, isopropenyl, 1-propenyl, 2-ethyl-1-propenyl, 1-methyl-1-propenyl, allyl, 2 -Methylpropenyl and 2-butenyl.

R12또는 R16에 표현된 C2-C4할로알케닐기의 예로는 2,2-디클로로에테닐, 2,2-디브로모에테닐, 3,3-디클로로알릴, 3,3-디브로모알릴, 2,3-디클로로알릴, 2,3-디브로모알릴, 2-클로로-2-프로페닐, 3-클로로-2-프로페닐, 2-브로모-2-프로페닐 및 3-클로로-2-부테닐이 있다.Examples of the C 2 -C 4 haloalkenyl group represented by R 12 or R 16 include 2,2-dichloroethenyl, 2,2-dibromoethenyl, 3,3-dichloroallyl, 3,3-dibromo Allyl, 2,3-dichloroallyl, 2,3-dibromoallyl, 2-chloro-2-propenyl, 3-chloro-2-propenyl, 2-bromo-2-propenyl and 3-chloro- 2-butenyl.

R1, R13또는 R14에 표현된 C3-C9알키닐기의 예로는 2-프로피닐, 1-메틸-2-프로피닐, 2-부티닐, 3-부티닐, 2-메틸-3-부티닐, 1-메틸-3-부티닐, 2-펜티닐, 4-펜티닐, 3-펜티닐, 1-에틸-2-프로피닐, 2-헥시닐, 3-헥시닐, 5-헥시닐, 1-펜틸-2-프로피닐 및 3-노니닐이 있다.Examples of C 3 -C 9 alkynyl groups represented by R 1 , R 13 or R 14 are 2-propynyl, 1-methyl-2-propynyl, 2-butynyl, 3-butynyl, 2-methyl-3 -Butynyl, 1-methyl-3-butynyl, 2-pentynyl, 4-pentynyl, 3-pentynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 5-hexyl Nil, 1-pentyl-2-propynyl and 3-noninyl.

R1, R13또는 R14에 표현된 C3-C5할로알키닐기의 예로는 3-클로로-2-프로피닐, 3-브로모-2-프로피닐, 4-클로로-2-부티닐, 3-클로로-1-메틸-2-프로피닐, 3-브로모-1-메틸-2-프로피닐, 4-클로로-3-부티닐, 4-브로모-3-부티닐, 4-클로로-2-메틸-3-부티닐, 4-브로모-2-메틸-3-부티닐, 1-메틸-4-클로로-3-부티닐, 1-메틸-4-브로모-3-부티닐, 5-클로로-4-펜티닐, 5-브로모-4-펜티닐, 1-에틸-3-클로로-2-프로피닐 및 1-에틸-3-브로모-2-프로피닐이 있다.Examples of C 3 -C 5 haloalkynyl groups represented by R 1 , R 13 or R 14 include 3-chloro-2-propynyl, 3-bromo-2-propynyl, 4-chloro-2-butynyl, 3-chloro-1-methyl-2-propynyl, 3-bromo-1-methyl-2-propynyl, 4-chloro-3-butynyl, 4-bromo-3-butynyl, 4-chloro- 2-methyl-3-butynyl, 4-bromo-2-methyl-3-butynyl, 1-methyl-4-chloro-3-butynyl, 1-methyl-4-bromo-3-butynyl, 5-chloro-4-pentynyl, 5-bromo-4-pentynyl, 1-ethyl-3-chloro-2-propynyl and 1-ethyl-3-bromo-2-propynyl.

R12또는 R16에 표현된 C2-C4알키닐기의 예로는 에티닐, 1-프로피닐, 2-프로피닐 및 1-메틸-2-프로피닐이 있다.Examples of C 2 -C 4 alkynyl groups represented by R 12 or R 16 are ethynyl, 1-propynyl, 2-propynyl and 1-methyl-2-propynyl.

R12또는 R16에 표현된 C2-C4할로알키닐기의 예로는 클로로에티닐, 브로모에티닐, 요오도에티닐, 3-클로로-2-프로피닐, 3-브로모-2-프로피닐, 3-요오도-2-프로피닐, 1-메틸-3-클로로-2-프로피닐, 1-메틸-3-브로모-2-프로피닐 및 1-메틸-3-요오도-2-프로피닐이 있다.Examples of the C 2 -C 4 haloalkynyl group represented by R 12 or R 16 include chloroethynyl, bromoethynyl, iodoethynyl, 3-chloro-2-propynyl, 3-bromo-2-propynyl , 3-iodo-2-propynyl, 1-methyl-3-chloro-2-propynyl, 1-methyl-3-bromo-2-propynyl and 1-methyl-3-iodo-2-propy There is Neil.

R12또는 R16에 표현된 C2-C4알키닐옥시기의 예로는 에티닐옥시, 1-프로피닐옥시, 2-프로피닐옥시 및 1-메틸-2-프로피닐옥시가 있다.Examples of C 2 -C 4 alkynyloxy groups represented by R 12 or R 16 are ethynyloxy, 1-propynyloxy, 2-propynyloxy and 1-methyl-2-propynyloxy.

R12또는 R16에 표현된 C2-C4할로알키닐옥시기의 예로는 클로로에티닐옥시, 3-클로로-2-프로피닐옥시, 3-브로모-2-프로피닐옥시, 1-메틸-3-클로로-2-프로피닐옥시 및 1-메틸-3-브로모-2-프로피닐옥시가 있다.Examples of the C 2 -C 4 haloalkynyloxy group represented by R 12 or R 16 include chloroethynyloxy, 3-chloro-2-propynyloxy, 3-bromo-2-propynyloxy, 1-methyl- 3-chloro-2-propynyloxy and 1-methyl-3-bromo-2-propynyloxy.

R1에 표현된 C2-C7알콕시알킬기의 예로는 메톡시메틸, 2-메톡시에틸, 에톡시메틸, 이소프로폭시메틸, 2-프로폭시메틸, 1-메톡시에틸, 2-에톡시에틸, 1-에톡시에틸, 3-메톡시프로필, 2-메톡시프로필, 1-메톡시프로필, 2-메톡시-2-메틸에틸, 2-프로폭시에틸, 2-에톡시프로필, 2-에톡시-1-메틸에틸, 2-메톡시부틸, 2-메톡시-1-에틸에틸, 3-에톡시프로필, 3-메톡시-n-부틸, 3-메톡시-2-메틸프로필-3-메톡시-1-메틸프로필, 2-이소프로폭시에틸, 3-메톡시부틸, 3-메틸-3-메톡시부틸, 2-부톡시에틸 및 2-부톡시-1-메틸에틸이 있다.Examples of the C 2 -C 7 alkoxyalkyl group represented by R 1 are methoxymethyl, 2-methoxyethyl, ethoxymethyl, isopropoxymethyl, 2-propoxymethyl, 1-methoxyethyl, 2-ethoxy Ethyl, 1-ethoxyethyl, 3-methoxypropyl, 2-methoxypropyl, 1-methoxypropyl, 2-methoxy-2-methylethyl, 2-propoxyethyl, 2-ethoxypropyl, 2- Ethoxy-1-methylethyl, 2-methoxybutyl, 2-methoxy-1-ethylethyl, 3-ethoxypropyl, 3-methoxy-n-butyl, 3-methoxy-2-methylpropyl-3 -Methoxy-1-methylpropyl, 2-isopropoxyethyl, 3-methoxybutyl, 3-methyl-3-methoxybutyl, 2-butoxyethyl and 2-butoxy-1-methylethyl.

R12에 표현된 C2-C4알콕시알킬기의 예로는 메톡시메틸, 에톡시메틸, n-프로폭시메틸, 이소프로폭시메틸, 2-메톡시에틸, 1-메톡시에틸, 2-에톡시에틸, 1-에톡시에틸, 3-메톡시프로필, 2-메톡시프로필, 1-메톡시프로필 및 2-메톡시-1-메틸에틸이 있다.Examples of the C 2 -C 4 alkoxyalkyl group represented by R 12 include methoxymethyl, ethoxymethyl, n-propoxymethyl, isopropoxymethyl, 2-methoxyethyl, 1-methoxyethyl, 2-ethoxy Ethyl, 1-ethoxyethyl, 3-methoxypropyl, 2-methoxypropyl, 1-methoxypropyl and 2-methoxy-1-methylethyl.

R1에 표현된 C2-C7알킬티오알킬기의 예로는 메틸티오메틸, 에틸티오메틸, 2-메틸티오에틸, 1-메틸티오에틸, 프로필티오메틸, 이소프로필티오메틸, 2-에틸티오에틸, 1-에틸티오에틸, 2-(메틸티오)프로필, 2-(메틸티오)프로필, 1-(메틸티오)프로필, 1-메틸-2-메틸티오에틸, 2-이소프로필티오에틸, 2-(프로필티오)에틸, 2-메틸티오-1-메틸프로필, 2-(메틸티오)부틸, 1-에틸-2-메틸티오에틸, 2-(에틸티오)프로필, 2-에틸티오-1-메틸에틸, 3-(에틸티오)프로필, 3-(메틸티오)부틸, 2-메틸-3-(메틸티오)프로필, 1-메틸-3-(메틸티오)프로필, 2-tert-부틸티오에틸, 2-이소부틸티오에틸, 2-sec-부틸티오에틸, 3-(tert-부틸티오)프로필, 3-(이소부틸티오)프로필 및 3-(sec-부틸티오)프로필이 있다.Examples of the C 2 -C 7 alkylthioalkyl group represented by R 1 are methylthiomethyl, ethylthiomethyl, 2-methylthioethyl, 1-methylthioethyl, propylthiomethyl, isopropylthiomethyl, 2-ethylthioethyl , 1-ethylthioethyl, 2- (methylthio) propyl, 2- (methylthio) propyl, 1- (methylthio) propyl, 1-methyl-2-methylthioethyl, 2-isopropylthioethyl, 2- (Propylthio) ethyl, 2-methylthio-1-methylpropyl, 2- (methylthio) butyl, 1-ethyl-2-methylthioethyl, 2- (ethylthio) propyl, 2-ethylthio-1-methyl Ethyl, 3- (ethylthio) propyl, 3- (methylthio) butyl, 2-methyl-3- (methylthio) propyl, 1-methyl-3- (methylthio) propyl, 2-tert-butylthioethyl, 2-isobutylthioethyl, 2-sec-butylthioethyl, 3- (tert-butylthio) propyl, 3- (isobutylthio) propyl and 3- (sec-butylthio) propyl.

R12에 표현된 C2-C4알킬티오알킬기의 예로는 메틸티오메틸, 에틸티오메틸, 프로필티오메틸, 이소프로필티오메틸, 2-메틸티오에틸, 1-메틸티오에틸, 2-에틸티오에틸, 1-에틸티오에틸, 3-메틸티오프로필, 2-메틸티오프로필, 1-메틸티오프로필 및 2-메틸티오-1-메틸에틸이 있다.Examples of the C 2 -C 4 alkylthioalkyl group represented by R 12 include methylthiomethyl, ethylthiomethyl, propylthiomethyl, isopropylthiomethyl, 2-methylthioethyl, 1-methylthioethyl, 2-ethylthioethyl , 1-ethylthioethyl, 3-methylthiopropyl, 2-methylthiopropyl, 1-methylthiopropyl and 2-methylthio-1-methylethyl.

R1에 표현된, C1-C4알킬, C1-C4알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 C3-C6시클로알킬기의 예로는 시클로프로필, 시클로부틸, 2-메톡시시클로펜틸, 2-에톡시시클로펜틸, 2-프로폭시시클로펜틸, 2-이소프로폭시시클로펜틸, 2-부톡시시클로펜틸, 2-이소부톡시시클로펜틸, 2-sec-부톡시시클로펜틸, 2-tert-부톡시시클로펜틸, 시클로펜틸, 3-메틸시클로펜틸, 2-메틸시클로펜틸, 3-메톡시시클로헥실, 3-에톡시시클로헥실, 3-프로폭시시클로헥실, 3-이소프로폭시시클로헥실, 3-부톡시시클로헥실, 3-이소부톡시시클로헥실, 3-sec-부톡시시클로헥실, 3-tert-부톡시시클로헥실, 4-메톡시시클로헥실, 4-에톡시시클로헥실, 4-프로폭시시클로헥실, 4-이소프로폭시시클로헥실, 4-부톡시시클로헥실, 4-이소부톡시시클로헥실, 4-sec-부톡시시클로헥실 및 4-tert-부톡시시클로헥실이 있다.Examples of C 3 -C 6 cycloalkyl groups which may be substituted with C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 1 -C 3 haloalkoxy represented by R 1 are cyclopropyl, cyclobutyl, 2- Methoxycyclopentyl, 2-ethoxycyclopentyl, 2-propoxycyclopentyl, 2-isopropoxycyclopentyl, 2-butoxycyclopentyl, 2-isobutoxycyclopentyl, 2-sec-butoxycyclopentyl, 2-tert-butoxycyclopentyl, cyclopentyl, 3-methylcyclopentyl, 2-methylcyclopentyl, 3-methoxycyclohexyl, 3-ethoxycyclohexyl, 3-propoxycyclohexyl, 3-isopropoxy Cyclohexyl, 3-butoxycyclohexyl, 3-isobutoxycyclohexyl, 3-sec-butoxycyclohexyl, 3-tert-butoxycyclohexyl, 4-methoxycyclohexyl, 4-ethoxycyclohexyl, 4 -Propoxycyclohexyl, 4-isopropoxycyclohexyl, 4-butoxycyclohexyl, 4-isobutoxycyclohexyl, 4-sec-butoxycyclohexyl and 4-tert-butoxy There are claw-hexyl.

R1에 표현된, C1-C4알킬로 치환될 수도 있는 C4-C9시클로알킬알킬기의 예로는 시클로프로필메틸, 시클로부틸메틸, 1-시클로프로필에틸, 2-메틸시클로프로판메틸, 2-(2-메틸시클로프로필)에틸, 시클로펜틸메틸, 시클로헥실메틸, 2-시클로헥실에틸, 3-시클로펜틸프로필 및 3-시클로헥실프로필이 있다.Examples of C 4 -C 9 cycloalkylalkyl groups which may be substituted with C 1 -C 4 alkyl represented by R 1 are cyclopropylmethyl, cyclobutylmethyl, 1-cyclopropylethyl, 2-methylcyclopropanemethyl, 2 -(2-methylcyclopropyl) ethyl, cyclopentylmethyl, cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclopentylpropyl and 3-cyclohexylpropyl.

R1에 표현된, C1-C4알킬로 치환될 수도 있는 C5-C6시클로알케닐기의 예로는 2-시클로헥세닐, 3,5,5-트리메틸-2-시클로헥세닐, 3-메틸-2-시클로헥세닐, 3-시클로헥세닐, 2-시클로펜테닐 및 3-시클로펜테닐이 있다.Examples of C 5 -C 6 cycloalkenyl groups, which may be substituted with C 1 -C 4 alkyl, represented by R 1 are 2-cyclohexenyl, 3,5,5-trimethyl-2-cyclohexenyl, 3- Methyl-2-cyclohexenyl, 3-cyclohexenyl, 2-cyclopentenyl and 3-cyclopentenyl.

R1에 표현된, C1-C4알킬로 치환될 수도 있는 C6-C8시클로알케닐알킬기의 예로는 (1-시클로펜테닐)메틸, (3-시클로헥세닐)메틸 및 2-(3-시클로헥세닐)에틸이 있다.Examples of C 6 -C 8 cycloalkenylalkyl groups which may be substituted with C 1 -C 4 alkyl represented by R 1 are (1-cyclopentenyl) methyl, (3-cyclohexenyl) methyl and 2- ( 3-cyclohexenyl) ethyl.

R12또는 R16에 표현된 C3-C6시클로알킬기의 예로는 시클로프로필, 시클로부틸, 시클로펜틸 및 시클로헥실이 있다.Examples of C 3 -C 6 cycloalkyl groups represented by R 12 or R 16 are cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

R12에 표현된 C5-C6시클로알케닐기의 예로는 1-시클로펜테닐, 2-시클로펜테닐, 3-시클로펜테닐, 1-시클로헥세닐, 2-시클로헥세닐 및 3-시클로헥세닐이 있다.Examples of C 5 -C 6 cycloalkenyl groups represented by R 12 include 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, 1-cyclohexenyl, 2-cyclohexenyl and 3-cyclohexen There is Senyl.

R12에 표현된 C3-C6시클로알킬옥시기의 예로는 시클로프로필옥시, 시클로부틸옥시, 시클로펜틸옥시 및 시클로헥실옥시가 있다.Examples of C 3 -C 6 cycloalkyloxy groups represented by R 12 are cyclopropyloxy, cyclobutyloxy, cyclopentyloxy and cyclohexyloxy.

R12에 표현된 C5-C6시클로알케닐옥시기의 예로는 1-시클로펜테닐옥시, 2-시클로펜테닐옥시, 3-시클로펜테닐옥시, 1-시클로헥세닐옥시, 2-시클로헥세닐옥시 및 3-시클로헥세닐옥시가 있다.Examples of the C 5 -C 6 cycloalkenyloxy group represented by R 12 include 1-cyclopentenyloxy, 2-cyclopentenyloxy, 3-cyclopentenyloxy, 1-cyclohexenyloxy, 2-cyclohexenyl Oxy and 3-cyclohexenyloxy.

R1또는 R12에 표현된 C1-C3알콕시기의 예로는 메톡시, 에톡시, n-프로폭시 및 이소프로폭시가 있다.Examples of C 1 -C 3 alkoxy groups represented by R 1 or R 12 are methoxy, ethoxy, n-propoxy and isopropoxy.

R12에 표현된 C1-C7알콕시기의 예로는 메톡시, 에톡시, 2-프로폭시, 이소프로폭시, n-부톡시, sec-부톡시, 이소부톡시, tert-부톡시, n-펜틸옥시, 이소펜틸옥시, 네오펜틸옥시, tert-펜틸옥시, (1-에틸프로필)옥시, n-헥실옥시 및 n-헵틸옥시가 있다.Examples of C 1 -C 7 alkoxy groups represented by R 12 are methoxy, ethoxy, 2-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, n- Pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy, (1-ethylpropyl) oxy, n-hexyloxy and n-heptyloxy.

R12또는 R16에 표현된, 혹은 R12또는 R16에 존재하는 C1-C3할로알콕시기의 예로는 트리플루오로메톡시, 디플루오로메톡시, 브로모디플루오로메톡시, 2-플루오로에톡시, 2,2,2-트리플루오로에톡시, 2-클로로에톡시, 2-브로모에톡시, 2-클로로-1,1,2-트리플루오로에톡시, 2-브로모-1,1,2-트리플루오로에톡시, 1,1,2,2-테트라플루오로에톡시, 1,2,2,3,3,3-헥사플루오로프로폭시, 3-플루오로-n-프로폭시, 3-클로로프로폭시, 3-브로모프로폭시, 2,2,3,3,3-펜타플루오로프로폭시, 3,3,3-트리플루오로프로폭시 및 1,1,2,2,2-펜타플루오로에톡시가 있다.Examples of the C 1 -C 3 haloalkoxy group present in R 12 or R 16 a, or R 12 or R 16 is present in the trifluoromethoxy, difluoromethoxy, bromo-modify difluoromethoxy, a 2-fluoro Methoxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-chloro-1,1,2-trifluoroethoxy, 2-bromo-1,1 , 2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 1,2,2,3,3,3-hexafluoropropoxy, 3-fluoro-n-propoxy , 3-chloropropoxy, 3-bromopropoxy, 2,2,3,3,3-pentafluoropropoxy, 3,3,3-trifluoropropoxy and 1,1,2,2, 2-pentafluoroethoxy.

R12또는 R16에 표현된 C1-C3알킬티오기의 예로는 메틸티오, 에틸티오, n-프로필티오 및 이소프로필티오가 있다.Examples of C 1 -C 3 alkylthio groups represented by R 12 or R 16 are methylthio, ethylthio, n-propylthio and isopropylthio.

R12또는 R16에 표현된 C1-C3할로알킬티오기의 에로는 트리플루오로에틸티오, 디플루오로메틸티오, 브로모디플루오로메틸티오, 2,2,2-트리플루오로에틸티오, 2-클로로-1,1,2-트리플루오로에틸티오, 2-브로모-1,1,2-트리플루오로에틸티오, 1,1,2,2-테트라플루오로에틸티오, 2-클로로에틸티오, 2-플루오로에틸티오, 2-브로모에틸티오, 3-플루오로프로필티오, 3-클로로-n-프로필티오, (3-브로모프로필)티오, 2,2,3,3,3-펜타플루오로프로필티오 및 3,3,3-트리플루오로프로필티오가 있다.Examples of the C 1 -C 3 haloalkylthio group represented by R 12 or R 16 include trifluoroethylthio, difluoromethylthio, bromodifluoromethylthio, 2,2,2-trifluoroethylthio , 2-chloro-1,1,2-trifluoroethylthio, 2-bromo-1,1,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2- Chloroethylthio, 2-fluoroethylthio, 2-bromoethylthio, 3-fluoropropylthio, 3-chloro-n-propylthio, (3-bromopropyl) thio, 2,2,3,3 , 3-pentafluoropropylthio and 3,3,3-trifluoropropylthio.

R12에 표현된 C3-C6알케닐옥시기의 예로는 알릴옥시, 2-메틸알릴옥시, 2-부테닐옥시, 3-메틸-2-부테닐옥시, 2-메틸-2-부테닐옥시, 2-펜테닐옥시 및 2-헥세닐옥시가 있다.Examples of the C 3 -C 6 alkenyloxy group represented by R 12 include allyloxy, 2-methylallyloxy, 2-butenyloxy, 3-methyl-2-butenyloxy, 2-methyl-2-butenyloxy , 2-pentenyloxy and 2-hexenyloxy.

R12에 표현된 C3-C6할로알케닐옥시기의 예로는 3,3-디시클로알릴옥시, 3,3-디브로모알릴옥시, 2,3-디클로로알릴옥시, 2,3-디브로모알릴옥시, 2-클로로-2-프로페닐옥시, 3-클로로-2-프로페닐옥시, 2-브로모-2-프로페닐옥시 및 3-클로로-2-부테닐옥시가 있다.Examples of the C 3 -C 6 haloalkenyloxy group represented by R 12 include 3,3-dicycloallyloxy, 3,3-dibromoallyloxy, 2,3-dichloroallyloxy, 2,3-dibro Molyloxy, 2-chloro-2-propenyloxy, 3-chloro-2-propenyloxy, 2-bromo-2-propenyloxy and 3-chloro-2-butenyloxy.

R12에 표현된 C1-C3히드록시알킬기의 예로는 히드록시메틸, 2-히드록시에틸, 1-히드록시에틸, 3-히드록시프로필, 2-히드록시프로필 및 1-히드록시프로필이 있다.Examples of C 1 -C 3 hydroxyalkyl groups represented by R 12 include hydroxymethyl, 2-hydroxyethyl, 1-hydroxyethyl, 3-hydroxypropyl, 2-hydroxypropyl and 1-hydroxypropyl have.

R12에 표현된 C2-C5알콕시카르보닐기의 예로는 메톡시카르보닐, 에톡시카르보닐, n-프로폭시카르보닐, 이소프로폭시카르보닐, n-부톡시카르보닐, 이소부톡시카르보닐, sec-부톡시카르보닐 및 tert-부톡시카르보닐이 있다.Examples of the C 2 -C 5 alkoxycarbonyl group represented by R 12 include methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl and tert-butoxycarbonyl.

R16에 표현된, 혹은 R1, R12또는 R16에 존재하는 C1-C4알킬기의 예로는 메틸, 에틸, n-프로필, 이소프로필, n-부틸, 이소부틸, sec-부틸 및 tert-부틸이 있다.Examples of C 1 -C 4 alkyl groups represented by R 16 or present in R 1 , R 12 or R 16 are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert -Butyl.

R16에 표현된, 또는 R16에 존재하는 C1-C4알콕시기의 예로는 메톡시, 에톡시, n-프로폭시, 이소프로폭시, n-부톡시, sec-부톡시, 이소부톡시 및 tert-부톡시가 있다.Examples of the C 1 -C 4 alkoxy group present in a R 16, or R 16 represent a methoxy, ethoxy, n- propoxy, isopropoxy, n- butoxy, sec- butoxy, isobutoxy and tert-butoxy.

R16에 표현된 C1-C2알킬술피닐기의 예로는 메틸술피닐 및 에틸술피닐이 있다.Examples of C 1 -C 2 alkylsulfinyl groups represented by R 16 are methylsulfinyl and ethylsulfinyl.

R16에 표현된 C1-C2알킬술포닐기의 예로는 메틸술피닐 및 에틸술포닐이 있다.Examples of C 1 -C 2 alkylsulfonyl groups represented by R 16 are methylsulfinyl and ethylsulfonyl.

R16에 표현된 C1-C2할로알킬술피닐기의 예로는 트리플루오로메틸술피닐, 2,2,2-트리플루오로에틸술피닐 및 퍼플루오로에틸술피닐이 있다.Examples of C 1 -C 2 haloalkylsulfinyl groups represented by R 16 are trifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl and perfluoroethylsulfinyl.

R16에 표현된 C1-C2할로알킬술포닐기의 예로는 트리플루오로메틸술포닐, 2,2,2-트리플루오로에틸술포닐 및 퍼플루오로에틸술포닐이 있다.Examples of C 1 -C 2 haloalkylsulfonyl groups represented by R 16 are trifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl and perfluoroethylsulfonyl.

R16에 표현된 (C1-C2알킬)아미노카르보닐기의 예로는 메틸아미노카르보닐 및 에틸아미노카르보닐이 있다.Examples of the (C 1 -C 2 alkyl) aminocarbonyl group represented by R 16 are methylaminocarbonyl and ethylaminocarbonyl.

R16에 표현된 [디(C1-C2알킬)아미노]카르보닐기의 예로는 디메틸아미노카르보닐, N-메틸-N-에틸아미노카르보닐 및 디에틸아미노카르보닐이 있다.Examples of the [di (C 1 -C 2 alkyl) amino] carbonyl group represented by R 16 are dimethylaminocarbonyl, N-methyl-N-ethylaminocarbonyl and diethylaminocarbonyl.

R1에 표현된, 치환될 수도 있는 복소환기의 복소환 고리의 예로는 1종 이상의 산소, 황 또는 질소 원자를 함유하는 5- 및 6-원 복소환 고리, 헥사메틸렌이민, 헵타메틸렌이민이 있다.Examples of heterocyclic rings of a heterocyclic group which may be substituted, represented by R 1 , include 5- and 6-membered heterocyclic rings containing one or more oxygen, sulfur or nitrogen atoms, hexamethyleneimine, heptamethyleneimine .

상기의 특정한 예로는 이속사졸, 이소티아졸, 티아졸, 1,3,4-티아디아졸, 피롤, 푸란, 티오펜, 피라졸, 이미다졸, 1,2,3-트리아졸, 1,2,4-트리아졸, 1,2,3,4-테트라졸, 피리딘, 피리다진, 피리미딘, 피라진, 1,2,4-트리아진, 1,3,5-트리아진, 인돌, 벤조디옥산, 피롤리딘, 2,3-디히드로-4H-피란-4-온, 크로몬, 모르폴린, 2-피롤린, 3-피롤린, 1,2,3,6-테트라히드로피롤리딘, 피페라진, 티오모르폴린, 티아졸리딘, 벤조푸란, 티아나프탈렌, 이미다졸, 벤즈이미다졸, 벤조트리아졸, 벤즈이속사졸, 벤족사졸, 벤조티아졸, 퀴놀린, 이소퀴놀린, 퀴녹살린, 퀴나졸, 피페리딘, 피페라진, 테트라히드로푸란, 테트라히드로피란 및 피라졸린이 있다.Specific examples of the above include isoxazole, isothiazole, thiazole, 1,3,4-thiadiazole, pyrrole, furan, thiophene, pyrazole, imidazole, 1,2,3-triazole, 1,2 , 4-triazole, 1,2,3,4-tetrazole, pyridine, pyridazine, pyrimidine, pyrazine, 1,2,4-triazine, 1,3,5-triazine, indole, benzodioxane , Pyrrolidine, 2,3-dihydro-4H-pyran-4-one, chromone, morpholine, 2-pyrroline, 3-pyrroline, 1,2,3,6-tetrahydropyrrolidine, Piperazine, thiomorpholine, thiazolidine, benzofuran, thianaphthalene, imidazole, benzimidazole, benzotriazole, benzisoxazole, benzoxazole, benzothiazole, quinoline, isoquinoline, quinoxaline, quinazole, Piperidine, piperazine, tetrahydrofuran, tetrahydropyran and pyrazoline.

하기는 본 발명에 의한 화합물의 바람직한 예이다:The following are preferred examples of the compounds according to the invention:

R13및 R14가 독립적으로 수소 또는 C1-C3알킬인 디할로프로펜 화합물;Dihalopropene compounds wherein R 13 and R 14 are independently hydrogen or C 1 -C 3 alkyl;

R1이 C1-C10알킬, C1-C5할로알킬, C2-C10알케닐, C2-C6할로알케닐, C3-C9알키닐 또는 C3-C5할로알키닐인 디할로프로펜 화합물;R 1 is C 1 -C 10 alkyl, C 1 -C 5 haloalkyl, C 2 -C 10 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 9 alkynyl or C 3 -C 5 haloalky Dihalopropene compound which is nil;

L이 C(=W)NR13인 디할로프로펜 화합물;Dihalopropene compound wherein L is C (= W) NR 13 ;

L이 WC(=W1)NR13이 디할로프로펜 화합물;L is WC (= W1) NR 13 is dihalopropene compound;

R1이 Q1, Q2, Q3또는 Q4이 디할로프로펜 화합물;R 1 is Q 1 , Q 2 , Q 3 or Q 4 is a dihalopropene compound;

R1이 Q1인 디할로프로펜 화합물;Dihalopropene compound wherein R 1 is Q 1 ;

R1은 Q1이고, L은 C=W, C(=W)NR13또는 SO2NR13인 디할로프로펜 화합물;R 1 is Q 1 and L is dihalopropene compound wherein C = W, C (= W) NR 13 or SO 2 NR 13 ;

R1은 Q1이고, L은 C(=W)NR13또는 SO2NR13이 디할로프로펜 화합물;R 1 is Q 1 , L is C (═W) NR 13 or SO 2 NR 13 is a dihalopropene compound;

R1은 Q1이고, L은 C(=W)NR13인 디할로프로펜 화합물;Dihalopropene compound wherein R 1 is Q 1 and L is C (═W) NR 13 ;

R1은 p=0인 Q1이고, L은 C=W, C(=W)NR13또는 SO2NR13인 디할로프로펜 화합물;R 1 is p = 0, and the Q 1, L is C = W, C (= W ) NR 13 or SO 2 NR 13 with the dihalo-propene compound;

R1은 p=0인 Q1이고, L은 C(=W)NR13또는 SO2NR13인 디할로프로펜 화합물;R 1 is p = 0, and the Q 1, L is C (= W) NR 13 or SO 2 NR 13 with the dihalo-propene compound;

R1은 p=0인 Q1이고, L은 C(=W)NR13인 디할로프로펜 화합물;R 1 is p = 0, and the Q 1, L is propene compound as a C (= W) NR 13-dihalo;

R2, R3및 R4가 독립적으로 할로겐 또는 C1-C3알킬인 디할로프로펜 화합물;Dihalopropene compounds wherein R 2 , R 3 and R 4 are independently halogen or C 1 -C 3 alkyl;

R2와 R3가 모두 염소이고, R4는 수소인 디할로프로펜 화합물;A dihalopropene compound in which both R 2 and R 3 are chlorine, and R 4 is hydrogen;

Y와 Z가 모두 산소인 디할로프로펜 화합물;Dihalopropene compounds in which Y and Z are both oxygen;

R5, R6및 R7이 독립적으로 수소 또는 C1-C3알킬인 디할로프로펜 화합물;Dihalopropene compounds wherein R 5 , R 6 and R 7 are independently hydrogen or C 1 -C 3 alkyl;

R5, R6및 R7이 모두 수소인 디할로프로펜 화합물.A dihalopropene compound wherein R 5 , R 6 and R 7 are all hydrogen.

하기는 본 발명에 의한 화합물의 또 다른 바람직한 예이다:The following is another preferred example of a compound according to the invention:

R1이 1종 이상의 산소, 황 또는 질소 원자를 함유하고 있는 5- 또는 6-원복소환기이고, (R16)s로 치환될 수도 있는 디할로프로펜 화합물; 및 좀 더 구체적으로, 5- 또는 6-원 복소환 기가 2-피라지닐, 2-인돌릴, 2-피롤릴, 2-퀴놀릴, 2-티에닐, 3-티에닐, 2-푸릴, 3-푸릴, 2-피리딜, 3-피리딜 또는 4-피리딜인 디할로프로펜 화합물;A dihalopropene compound wherein R 1 is a 5- or 6-membered heterocyclic group containing one or more oxygen, sulfur or nitrogen atoms, and which may be substituted with (R 16 ) s ; And more specifically, a 5- or 6-membered heterocyclic group is 2-pyrazinyl, 2-indolyl, 2-pyrrolyl, 2-quinolyl, 2-thienyl, 3-thienyl, 2-furyl, 3 Dihalopropene compound which is furyl, 2-pyridyl, 3-pyridyl or 4-pyridyl;

5- 또는 6-원 복소환 기가 2-피라지닐, 2-인돌릴, 2-피롤릴, 2-퀴놀릴, 2-티에닐, 3-티에닐, 2-푸릴, 3-푸릴, 2-피리딜, 3-피리딜 또는 4-피리딜이고, L이 C=W, C(=W)NR13또는 SO2NR13인 디할로프로펜 화합물;5- or 6-membered heterocyclic groups are 2-pyrazinyl, 2-indolyl, 2-pyrrolyl, 2-quinolyl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-pyri Dihalopropene compound wherein diyl, 3-pyridyl or 4-pyridyl and L is C = W, C (= W) NR 13 or SO 2 NR 13 ;

5- 또는 6-원 복소환 기가 2-피라지닐, 2-인돌릴, 2-피롤릴, 2-퀴놀릴, 2-티에닐, 3-티에닐, 2-푸릴, 3-푸릴, 2-피리딜, 3-피리딜 또는 4-피리딜이고, L이 C(=W)NR13또는 SO2NR13인 디할로프로펜 화합물;5- or 6-membered heterocyclic groups are 2-pyrazinyl, 2-indolyl, 2-pyrrolyl, 2-quinolyl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-pyri Dihalopropene compound wherein diyl, 3-pyridyl or 4-pyridyl and L is C (= W) NR 13 or SO 2 NR 13 ;

5- 또는 6-원 복소환 기가 2-피라지닐, 2-인돌릴, 2-피롤릴, 2-퀴놀릴, 2-티에닐, 3-티에닐, 2-푸릴, 3-푸릴, 2-피리딜, 3-피리딜 또는 4-피리딜이고, L이 C(=W)NR13인 디할로프로펜 화합물; 및5- or 6-membered heterocyclic groups are 2-pyrazinyl, 2-indolyl, 2-pyrrolyl, 2-quinolyl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-pyri Dihalopropene compound wherein diyl, 3-pyridyl or 4-pyridyl and L is C (= W) NR 13 ; And

5- 또는 6-원 복소환 기가 1-피롤리디닐 또는 1-피페리딜이고, L이 C=W인 디할로프로펜 화합물.A dihalopropene compound wherein the 5- or 6-membered heterocyclic group is 1-pyrrolidinyl or 1-piperidyl and L is C = W.

본 발명에 의한 화합물은 예컨대 하기의 제조 공정 A-N에 의해 제조할 수 있다.The compound according to the present invention can be produced, for example, by the following preparation step A-N.

(제조 공정 A)(Manufacturing Process A)

이 공정에서, 하기 화학식(5)의 화합물을 하기 화학식(6)의 화합물과 반응시킨다:In this process, a compound of formula (5) is reacted with a compound of formula (6):

[화학식 5][Formula 5]

[식중, R1, R2, R3, R4, R5, R6, R7, L, Y, Z, m 및 n은 각각 상기 정의와 같다][Wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , L, Y, Z, m and n are the same as defined above]

[화학식 6][Formula 6]

L2-CH2CH=CX2 L 2 -CH 2 CH = CX 2

[식중, X는 상기 정의와 같고, L2는 할로겐(예, 염소, 브롬, 요오드), 메실옥시 또는 토실옥시이다].Wherein X is as defined above and L 2 is halogen (eg chlorine, bromine, iodine), mesyloxy or tosyloxy].

반응은 적절한 염기의 존재하에 불활성 용매중에서 바람직하게 진행된다.The reaction proceeds preferably in an inert solvent in the presence of a suitable base.

사용될 수 있는 용매의 예로는 아세톤, 메틸 에틸 케톤, 시클로헥사논 등의 케톤; 1,2-디메톡시에탄, 테트라히드로푸란, 디옥산, 디알킬(예, C1-C4)에테르(예, 디에틸 에테르, 디이소프로필 에테르) 등의 에테르; N,N-디메틸포름아미드, 디메틸술폭시드, 헥사메틸포스포릭 트리아미드, 술포란, 아세토니트릴, 니트로메탄; 디클로로메탄, 클로로포름, 1,2-디클로로에탄, 클로로벤젠 등의 할로겐화된 탄화수소; 톨루엔, 벤젠, 크실렌 등의 탄화수소; 및 물이 있다. 필요한 경우, 상기 용매의 혼합물이 사용될 수 있다.Examples of the solvent that can be used include ketones such as acetone, methyl ethyl ketone and cyclohexanone; Ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane, dialkyl (e.g., C 1 -C 4 ) ethers (e.g., diethyl ether, diisopropyl ether); N, N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, acetonitrile, nitromethane; Halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane and chlorobenzene; Hydrocarbons such as toluene, benzene and xylene; And water. If necessary, mixtures of these solvents can be used.

사용될 수 있는 염기의 예로는 알칼리 금속 또는 알칼리 토금속의 수산화물, 예컨대 수산화 리튬, 수산화 나트륨, 수산화 칼륨 및 수산화 칼슘; 알칼리 금속 또는 알칼리 토금속의 탄산염, 예컨대 탄산 리튬, 탄산 칼륨, 탄산 나트륨 및 탄산칼슘; 알칼리 금속 또는 알칼리 토금속의 수소화물, 예컨대 수소화 리튬, 수소화 나트륨, 수소화 칼륨 및 수소화 칼슘; 알칼리 금속 알콕시드(예, C1-C4), 예컨대 소듐 메톡시드, 소듐 에톡시드 및 포타슘 tert-부톡시드; 및 유기 염기, 예컨대 트리에틸아민 및 피리딘이 있다. 필요할 경우, 암모늄 염(예, 벤질트리에틸암모늄 클로라이드)과 같은 촉매를, 화학식(5)의 화합물 1몰 당 0.01 내지 1몰의 비율로 반응계에 첨가할 수 있다.Examples of bases that can be used include hydroxides of alkali or alkaline earth metals such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide; Carbonates of alkali or alkaline earth metals such as lithium carbonate, potassium carbonate, sodium carbonate and calcium carbonate; Hydrides of alkali or alkaline earth metals such as lithium hydride, sodium hydride, potassium hydride and calcium hydride; Alkali metal alkoxides (eg C 1 -C 4 ) such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; And organic bases such as triethylamine and pyridine. If necessary, a catalyst such as an ammonium salt (eg benzyltriethylammonium chloride) can be added to the reaction system at a rate of 0.01 to 1 mole per mole of the compound of formula (5).

반응 온도는 일반적으로 -20℃ 내지 +150℃의 범위 또는 반응에 사용된 용매의 비점으로 맞추며, 바람직하게는 -5℃ 내지 +100℃ 또는 반응에 사용된 용매의 비점으로 맞춘다.The reaction temperature is generally set in the range of −20 ° C. to + 150 ° C. or at the boiling point of the solvent used in the reaction, preferably at −5 ° C. to + 100 ° C. or at the boiling point of the solvent used in the reaction.

반응에 사용되는 출발 물질과 염기의 몰비는 자유롭게 결정할 수 있으나, 동 몰비로 또는 그에 근접한 비로 하는 것이 반응에 유리하다.The molar ratio of the starting material and the base used in the reaction can be freely determined, but it is advantageous for the reaction to be at or close to the molar ratio.

반응이 종결된 후, 반응 혼합물을 유기 용매 추출, 농축 등의 통상적인 후-처리를 시켜, 본 발명의 목적하는 화합물을 분리할 수 있다. 또한 필요할 경우, 크로마토그래피, 증류 또는 재결정과 같은 통상적인 기술에 의해 정제할 수 있다.After the reaction is completed, the reaction mixture can be subjected to conventional post-treatment such as organic solvent extraction, concentration, etc. to separate the desired compound of the present invention. If necessary, it can also be purified by conventional techniques such as chromatography, distillation or recrystallization.

(Y가 산소인, 본 발명에 의한 화합물의 제조 공정 B)(Production process B of a compound according to the invention, wherein Y is oxygen)

이 공정에서는 화학식 (5)의 화합물을 하기 화학식(7)의 알코올 화합물과 반응시킨다:In this process, the compound of formula (5) is reacted with an alcohol compound of formula (7):

[화학식 7][Formula 7]

HO-CH2CH=CX2 HO-CH 2 CH = CX 2

[식중, X는 상기 정의와 같다][Wherein X is as defined above]

필요할 경우, 반응은 불활성 용매중의 적절한 탈수제의 존재하에서 바람직하게 진행된다.If necessary, the reaction proceeds preferably in the presence of a suitable dehydrating agent in an inert solvent.

사용될 수 있는 탈수제의 예로는 디시클로헥실카르보디이미드, 및 디알킬(예, C1-C4)아조디카르복실레이트(예, 디에틸아조디카르복실레이트, 디이소프로필아조디카르복실레이트)-트리알킬(예, C1-C20)포스핀 또는 트리아릴포스핀(예, 트리페닐포스핀, 트리옥틸포스핀, 트리부틸포스핀)이 있다.Examples of dehydrating agents that can be used are dicyclohexylcarbodiimide, and dialkyl (eg C 1 -C 4 ) azodicarboxylates (eg diethylazodicarboxylate, diisopropylazodidicarboxylate) ) -Trialkyl (eg C 1 -C 20 ) phosphine or triarylphosphine (eg triphenylphosphine, trioctylphosphine, tributylphosphine).

사용될 수 있는 용매의 예로는 탄화수소, 예컨대 벤젠, 크실렌 및 톨루엔; 에테르, 예컨대 디에틸 에테르, 디이소프로필 에테르, 테트라히드로푸란 및 디옥산; 및 할로겐화된 탄화수소, 예컨대 사염화 탄소, 디클로로메탄, 클로로벤젠 및 디클로로벤젠이 있다.Examples of solvents that can be used include hydrocarbons such as benzene, xylene and toluene; Ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran and dioxane; And halogenated hydrocarbons such as carbon tetrachloride, dichloromethane, chlorobenzene and dichlorobenzene.

반응 온도는 통상 -20℃ 내지 +200℃의 범위 또는 반응에 사용되는 용매의 비점으로 맞춘다.The reaction temperature is usually set in the range of -20 ° C to + 200 ° C or the boiling point of the solvent used in the reaction.

반응에 사용되는 출발물질과 탈수제의 몰비는 자유롭게 결정될 수 있으나, 동몰비로 또는 그에 근접한 비로 반응에 적용하는 것이 유리하다.The molar ratio of starting material and dehydrating agent used in the reaction can be freely determined, but it is advantageous to apply to the reaction at or near equimolar ratios.

반응이 종결된 후, 반응 혼합물을 유기 용매 추출, 농축 등의 통상적인 후-처리를 시켜, 본 발명의 목적하는 화합물을 분리할 수 있다. 또한 필요할 경우, 크로마토그래피, 증류 또는 재결정과 같은 통상적인 기술에 의해 정제할 수 있다.After the reaction is completed, the reaction mixture can be subjected to conventional post-treatment such as organic solvent extraction, concentration, etc. to separate the desired compound of the present invention. If necessary, it can also be purified by conventional techniques such as chromatography, distillation or recrystallization.

(Y가 산소인, 본 발명에 의한 화합물의 제조 공정 C)(Production process C of a compound according to the invention, wherein Y is oxygen)

이 공정에서는, 하기 화학식(8)의 알데히드를 사염화 탄소 또는 사브롬화 탄소와 반응시킨다:In this process, the aldehyde of formula (8) is reacted with carbon tetrachloride or carbon tetrabromide:

[화학식 8][Formula 8]

[식중, R1, R2, R3, R4, R5, R6, R7, L, Z, m 및 n은 각각 상기 정의와 같다].[Wherein, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , L, Z, m and n are the same as defined above, respectively].

반응은, 불활성 용매중에서 적절한 트리알킬포스핀 또는 트리아릴포스핀의 존재하에, 그리고 필요할 경우 금속 아연의 존재하에서 바람직하게 진행된다.The reaction proceeds preferably in the presence of a suitable trialkylphosphine or triarylphosphine in an inert solvent and, if necessary, in the presence of metal zinc.

사용될 수 있는 용매의 예로는 탄화수소, 예컨대 벤젠, 크실렌 및 톨루엔; 에테르, 예컨대 디에틸 에테르, 디이소프로필 에테르, 테트라히드로푸란 및 디옥산; 및 할로겐화된 탄화수소(사염화 탄소와 사브롬화 탄소는 제외), 예컨대 디클로로메탄, 1,2-디클로로에탄 및 클로로벤젠이 있다.Examples of solvents that can be used include hydrocarbons such as benzene, xylene and toluene; Ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran and dioxane; And halogenated hydrocarbons (excluding carbon tetrachloride and carbon tetrabromide) such as dichloromethane, 1,2-dichloroethane and chlorobenzene.

반응 온도는 통상 -30℃ 내지 +150℃의 범위 또는 반응에 사용되는 용매의 비점으로 맞춘다.The reaction temperature is usually set in the range of -30 ° C to + 150 ° C or the boiling point of the solvent used in the reaction.

반응에 사용될 수 있는 트리알킬(예, C1-C20) 포스핀 또는 트리아릴포스핀의 예로는 트리페닐포스핀과 트리옥틸포스핀이 있다. 필요할 경우 사용되는 금속아연은 분진의 형태가 바람직하다.Examples of trialkyl (eg C 1 -C 20 ) phosphines or triarylphosphines that can be used in the reaction include triphenylphosphine and trioctylphosphine. The metal zinc used when necessary is preferably in the form of dust.

반응에 사용되는 출발물질과 시약의 몰비는 자유롭게 결정될 수 있으나, 사브롬화 또는 사염화 탄소, 트리알킬포스핀 또는 트리아릴포스핀, 및 아연은 화학식(8)의 알데히드 화합물 1몰 당 각각, 2몰, 2 내지 4몰(아연이 사용될 경우 2몰), 및 2몰이거나 그에 근접한 비로 반응에 적용하는 것이 유리하다.The molar ratio of starting material and reagent used in the reaction can be freely determined, but carbon tetrabromide or tetrachloride, trialkylphosphine or triarylphosphine, and zinc are each 2 moles per mole of aldehyde compound of formula (8), It is advantageous to apply to the reaction in a ratio of 2 to 4 moles (2 moles when zinc is used), and a ratio of or close to 2 moles.

반응이 종결된 후, 반응 혼합물을 유기 용매 추출, 농축 등의 통상적인 후-처리를 시켜, 본 발명의 목적하는 화합물을 분리할 수 있다. 또한 필요할 경우, 크로마토그래피, 증류 또는 재결정과 같은 통상적인 기술에 의해 정제할 수 있다.After the reaction is completed, the reaction mixture can be subjected to conventional post-treatment such as organic solvent extraction, concentration, etc. to separate the desired compound of the present invention. If necessary, it can also be purified by conventional techniques such as chromatography, distillation or recrystallization.

(Y와 Z가 모두 산소인, 본 발명에 의한 화합물의 제조 공정 D)(Production process D of compound according to the invention, wherein Y and Z are both oxygen)

이 공정에서는, 하기 화학식(9)의 화합물을 하기 화학식(10)의 화합물과 반응시킨다:In this process, a compound of formula (9) is reacted with a compound of formula (10):

[화학식 9][Formula 9]

[식중, R2, R3, R4, X 및 n은 각각 상기 정의와 같다][Wherein R 2 , R 3 , R 4 , X and n are the same as defined above]

[화학식 10][Formula 10]

[식중, R1, R5, R6, R7, L, L2, 및 m은 각각 상기 정의와 같다][Wherein R 1 , R 5 , R 6 , R 7 , L, L 2 , and m are the same as defined above, respectively]

반응은, 불활성 용매중에서 적절한 염기의 존재하에서 바람직하게 진행된다.The reaction proceeds preferably in the presence of a suitable base in an inert solvent.

사용될 수 있는 용매의 예로는 케톤, 예컨대 아세톤, 메틸 에틸 케톤 및 시클로헥사논; 에테르, 예컨대 1,2-디메톡시에탄, 테트라히드로푸란, 디옥산 및 디알킬(예, C1-C4)에테르(예, 디에틸 에테르, 디이소프로필 에테르); N,N-디메틸포름아미드, 디메틸술폭시드, 헥사메틸포스포릭 트리아미드, 술포란, 아세토니트릴, 니트로메탄; 할로겐화된 탄화수소, 예컨대 디클로로메탄, 클로로포름, 1,2-디클로로에탄 및 클로로벤젠; 탄화수소, 예컨대 톨루엔, 벤젠 및 크실렌; 및 물이 있다. 필요한 경우, 상기 용매의 혼합물이 사용될 수 있다.Examples of solvents that can be used include ketones such as acetone, methyl ethyl ketone and cyclohexanone; Ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane and dialkyl (eg C 1 -C 4 ) ethers (eg diethyl ether, diisopropyl ether); N, N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, acetonitrile, nitromethane; Halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane and chlorobenzene; Hydrocarbons such as toluene, benzene and xylene; And water. If necessary, mixtures of these solvents can be used.

사용될 수 있는 염기의 예로는 알칼리 금속 또는 알칼리 토금속의 수산화물, 예컨대 수산화 리튬, 수산화 나트륨, 수산화 칼륨 및 수산화 칼슘; 알칼리 금속 또는 알칼리 토금속의 탄산염, 예컨대 탄산 리튬, 탄산 칼륨, 탄산 나트륨 및 탄산칼슘; 알칼리 금속 또는 알칼리 토금속의 수소화물, 예컨대 수소화 리튬, 수소화 나트륨, 수소화 칼륨 및 수소화 칼슘; 알칼리 금속 알콕시드(예, C1-C4), 예컨대 소듐 메톡시드, 소듐 에톡시드 및 포타슘 tert-부톡시드; 및 유기 염기, 예컨대 트리에틸아민 및 피리딘이 있다 .필요한 경우, 암모늄 염(예, 벤질트리에틸암모늄클로라이드)과 같은 촉매를, 화학식(9)의 화합물 1몰 당 0.01 내지 1몰의 비율로 반응계에 첨가할 수 있다.Examples of bases that can be used include hydroxides of alkali or alkaline earth metals such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide; Carbonates of alkali or alkaline earth metals such as lithium carbonate, potassium carbonate, sodium carbonate and calcium carbonate; Hydrides of alkali or alkaline earth metals such as lithium hydride, sodium hydride, potassium hydride and calcium hydride; Alkali metal alkoxides (eg C 1 -C 4 ) such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; And organic bases such as triethylamine and pyridine. If necessary, a catalyst such as an ammonium salt (e.g., benzyltriethylammonium chloride) is added to the reaction system at a rate of 0.01 to 1 mole per mole of the compound of formula (9). Can be added.

반응 온도는 일반적으로 -20℃ 내지 +150℃의 범위 또는 반응에 사용된 용매의 비점으로 맞추며, 바람직하게는 -5℃ 내지 +100℃ 또는 반응에 사용된 용매의 비점으로 맞춘다.The reaction temperature is generally set in the range of −20 ° C. to + 150 ° C. or at the boiling point of the solvent used in the reaction, preferably at −5 ° C. to + 100 ° C. or at the boiling point of the solvent used in the reaction.

반응에 사용되는 출발 물질과 탈수제의 몰비는 자유롭게 결정할 수 있으나, 동몰비로 또는 그에 근접한 비로 하는 것이 반응에 유리하다.The molar ratio of the starting material and the dehydrating agent used in the reaction can be freely determined, but it is advantageous for the reaction to be at or near the equimolar ratio.

반응이 종결된 후, 반응 혼합물을 유기 용매 추출, 농축 등의 통상적인 후- 처리를 시켜, 본 발명의 목적하는 화합물을 분리할 수 있다. 또한 필요할 경우, 크로마토그래피, 증류 또는 재결정과 같은 통상적인 기술에 의해 정제할 수 있다.After the reaction is completed, the reaction mixture can be subjected to conventional post-treatment such as organic solvent extraction, concentration, etc. to separate the desired compound of the present invention. If necessary, it can also be purified by conventional techniques such as chromatography, distillation or recrystallization.

(Y와 Z가 모두 산소인, 본 발명에 의한 화합물의 제조 공정 E)(Production process E of a compound according to the invention, wherein Y and Z are both oxygen)

이 공정에서는, 화학식(9)의 화합물을 하기 화학식(11)의 알코올 화합물과 반응시킨다:In this process, the compound of formula (9) is reacted with an alcohol compound of formula (11):

[화학식 11][Formula 11]

[식중, R1, R5, R6, R7, L 및 m은 각각 상기 정의와 같다].[Wherein, R 1 , R 5 , R 6 , R 7 , L and m are the same as defined above, respectively].

필요할 경우, 반응은 불활성 용매중의 적절한 탈수제의 존재하에서 바람직하게 진행된다.If necessary, the reaction proceeds preferably in the presence of a suitable dehydrating agent in an inert solvent.

사용될 수 있는 탈수제의 예로는 디시클로헥실카르보디이미드, 및 디알킬(예, C1-C4)아조디카르복실레이트(예, 디에틸아조디카르복실레이트, 디이소프로필아조디카르복실레이트)-트리알킬(예, C1-C20)포스핀 또는 트리아릴포스핀(예, 트리페닐포스핀, 트리옥틸포스핀, 트리부틸포스핀)이 있다.Examples of dehydrating agents that can be used are dicyclohexylcarbodiimide, and dialkyl (eg C 1 -C 4 ) azodicarboxylates (eg diethylazodicarboxylate, diisopropylazodidicarboxylate) ) -Trialkyl (eg C 1 -C 20 ) phosphine or triarylphosphine (eg triphenylphosphine, trioctylphosphine, tributylphosphine).

사용될 수 있는 용매의 예로는 탄화수소, 예컨대 벤젠, 크실렌 및 톨루엔; 에테르, 예컨대 디에틸 에테르, 디이소프로필 에테르, 테트라히드로푸란 및 디옥산; 및 할로겐화된 탄화수소, 예컨대 사염화 탄소, 디클로로메탄, 클로로벤젠 및 디클로로벤젠이 있다.Examples of solvents that can be used include hydrocarbons such as benzene, xylene and toluene; Ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran and dioxane; And halogenated hydrocarbons such as carbon tetrachloride, dichloromethane, chlorobenzene and dichlorobenzene.

반응 온도는 통상 -20℃ 내지 +200℃의 범위 또는 반응에 사용되는 용매의 비점으로 맞춘다.The reaction temperature is usually set in the range of -20 ° C to + 200 ° C or the boiling point of the solvent used in the reaction.

반응에 사용되는 물질과 탈수제의 몰비는 자유롭게 결정될 수 있으나, 동물비로 또는 그에 근접한 비로 반응에 적용하는 것이 유리하다.The molar ratio of the material used for the reaction and the dehydrating agent can be freely determined, but it is advantageous to apply to the reaction in an animal ratio or at a ratio close thereto.

반응이 종결된 후, 반응 혼합물을 유기 용매 추출, 농축 등의 통상적인 후- 처리를 시켜, 본 발명의 목적하는 화합물을 분리할 수 있다. 또한 필요할 경우, 크로마토그래피, 증류 또는 재결정과 같은 통상적인 기술에 의해 정제할 수 있다.After the reaction is completed, the reaction mixture can be subjected to conventional post-treatment such as organic solvent extraction, concentration, etc. to separate the desired compound of the present invention. If necessary, it can also be purified by conventional techniques such as chromatography, distillation or recrystallization.

(L이 -C(=O)NR13인, 본 발명에 의한 화합물의 제조 공정 F)(Step F) for preparing a compound according to the present invention, wherein L is -C (= O) NR 13

이 공정에서는, 하기 화학식(12)의 아민 화합물을 하기 화학식(13)의 카르복실산 화합물과 반응시킨다:In this process, the amine compound of formula (12) is reacted with the carboxylic acid compound of formula (13):

[화학식 12][Formula 12]

[식중, R2, R3, R4, R5, R6, R7, R13, X, Y, Z, m 및 n은 각각 상기 정의와 같다][Wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 13 , X, Y, Z, m and n are the same as defined above]

[화학식 13][Formula 13]

R1-C(=O)-VR1-C (= O) -V

[식중, R1은 각각 상기 정의와 같고, V는 염소, 브롬, 히드록실, 메톡시, 에톡시, 프로폭시 또는 1-이미다졸릴이다].Wherein each R 1 is as defined above and V is chlorine, bromine, hydroxyl, methoxy, ethoxy, propoxy or 1-imidazolyl.

(i) 화학식(13)의 V가 염소, 브롬 또는 1-이미다졸릴일 경우, 사용될 수 있는 용매의 예로는 에테르, 예컨대 디에틸 에테르, 테트라히드로푸란, 디옥산 등; 방향족 탄화수소, 예컨대 벤젠, 톨루엔, 크실렌, 클로로벤젠, 피리딘 등; 탄화수소, 예컨대 n-헥산, n-헵탄, 시클로헥산 등; 할로겐화된 탄화수소, 예컨대 메틸렌클로라이드, 클로로포름, 사염화 탄소, 1, 2-디클르로에탄 등; 에스테르, 예컨대 에틸 아세테이트, 메틸 아세테이트 등; 물; 니트릴, 예컨대 아세토니트릴; 극성 용매, 예컨대 N,N-디메틸포름아미드, N,N-디메틸아세트아미드, N-메틸피롤리돈, 디메틸술폭시드 등; 및 그의 혼합물이 있다.(i) When V in formula (13) is chlorine, bromine or 1-imidazolyl, examples of solvents that may be used include ethers such as diethyl ether, tetrahydrofuran, dioxane and the like; Aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, pyridine and the like; Hydrocarbons such as n-hexane, n-heptane, cyclohexane and the like; Halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1, 2-dichloroethane and the like; Esters such as ethyl acetate, methyl acetate and the like; water; Nitriles such as acetonitrile; Polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide and the like; And mixtures thereof.

반응 온도는 통상 -20℃ 내지 +150℃의 범위 또는 반응에 사용되는 용매의 비점으로 맞추며, 바람직하게는 0℃ 내지 50℃로 맞춘다.The reaction temperature is usually set in the range of -20 ° C to + 150 ° C or the boiling point of the solvent used in the reaction, and preferably at 0 ° C to 50 ° C.

반응은 통상적으로, 화학식(13)의 화합물 1몰 당 1 내지 10몰의 몰비의 염기, 예컨대 수산화 나트륨, 수산화 칼륨, 탄산 나트륨, 탄산 칼륨, 트리에틸아민 또는 피리딘의 존재하에서 바람직하게 진행된다.The reaction usually proceeds preferably in the presence of a molar ratio of 1 to 10 moles of base per mole of the compound of formula (13), such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine or pyridine.

용매로서 물을 사용하여 2상 반응을 수행하는 경우, 테트라-n-부틸암모늄브로마이드 또는 벤질트리에틸암모늄 클로라이드 등의 상전이 촉매를 사용하여 반응 속도를 증가시킬 수 있다.When the two-phase reaction is carried out using water as the solvent, a phase transfer catalyst such as tetra-n-butylammonium bromide or benzyltriethylammonium chloride can be used to increase the reaction rate.

(ii) 화학식(13)의 V가 히드록실, 메톡시, 에톡시 또는 프로폭시일 경우, 반응은 통상 용매 없이, 또는 N,N-디메틸포름아미드, N,N-디메틸아세트아미드, N-메틸피롤리돈, 디메틸술폭시드 등의 극성 용매, 혹은 벤젠, 톨루엔, 크실렌, 클로로벤젠 등의 방향족 탄화수소 용매중에서, 50℃ 내지 250℃의 반응 온도로 진행된다.(ii) when V of formula (13) is hydroxyl, methoxy, ethoxy or propoxy, the reaction is usually without solvent or with N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl In polar solvents, such as pyrrolidone and dimethyl sulfoxide, or aromatic hydrocarbon solvents, such as benzene, toluene, xylene, and chlorobenzene, it advances to reaction temperature of 50 degreeC-250 degreeC.

필요할 경우, 반응 촉매로서, 황산, 벤젠술폰산, p-톨루엔술폰산, 활성 실리카겔 등의 산성 물질, 또는 피리딘, 트리에틸아민, 소듐 메톡시드, 소듐 에톡시드, 활성 알루미나 등의 염기성 물질이 화학식(13)의 카르복실산 화합물의 중량에 대해 0.0001 내지 1배의 중량비로 사용될 수 있다.If necessary, as a reaction catalyst, an acidic substance such as sulfuric acid, benzenesulfonic acid, p-toluenesulfonic acid, activated silica gel, or a basic substance such as pyridine, triethylamine, sodium methoxide, sodium ethoxide, activated alumina, etc. It may be used in a weight ratio of 0.0001 to 1 times the weight of the carboxylic acid compound of.

반응에 사용되는 물질과 탈수제의 몰비는 자유롭게 결정할 수 있으나, 동물비로 또는 그에 근접한 비로 사용하는 것이 유리하다.The molar ratio of the material used for the reaction and the dehydrating agent can be freely determined, but it is advantageous to use it at or close to the animal ratio.

(iii) 화학식(13)의 V가 히드록실일 경우, 하기의 제조 공정이 사용될 수 있다.(iii) When V in formula (13) is hydroxyl, the following preparation process can be used.

즉, 화학식(13)의 카르복실산 화합물을 통상 불활성 용매의 존재하에 또는 용매 없이 화학식(12)의 아민 화합물과 반응시켜, 탈수 축합에 의해 목적하는 본 발명의 화합물을 수득한다. 탈수제의 에로는 카르보디이미드, 예컨대 디시클로헥실카르보디이미드, 1-에틸-3-(3-디메틸아미노프로필)카르보디이미드; 및 무기 탈수제, 예컨대 사염화 규소가 있다. 불활성 유기 용매의 예로는 비-방향족 탄화수소, 예컨대 n-펜탄, n-헥산, n-헵탄, 시클로헥산 등; 방향족 탄화수소, 예컨대 벤젠, 톨루엔, 크실렌 등; 염소화된 탄화수소, 예컨대 메틸렌 클로라이드, 클로로포름, 사염화 탄소, 1,2-디클로로에탄, 클로로벤젠, o-디클로로벤젠 등; 에스테르, 예컨대 에틸 아세테이트, 메틸 아세테이트 등; 아미드, 예컨대 N,N-디메틸포름아미드, N,N-디메틸아세트아미드, N-메틸피롤리돈 등; 니트릴, 예컨대 아세토니트릴; 에테르, 예컨대 디에틸 에테르, 테트라히드로푸란, 디옥산 등; 및 피리딘이 있다.That is, the carboxylic acid compound of formula (13) is usually reacted with the amine compound of formula (12) in the presence or absence of an inert solvent to obtain the desired compound of the present invention by dehydration condensation. Examples of dehydrating agents include carbodiimides such as dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide; And inorganic dehydrating agents such as silicon tetrachloride. Examples of inert organic solvents include non-aromatic hydrocarbons such as n-pentane, n-hexane, n-heptane, cyclohexane and the like; Aromatic hydrocarbons such as benzene, toluene, xylene and the like; Chlorinated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, o-dichlorobenzene and the like; Esters such as ethyl acetate, methyl acetate and the like; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and the like; Nitriles such as acetonitrile; Ethers such as diethyl ether, tetrahydrofuran, dioxane and the like; And pyridine.

반응 온도는 통상 -20℃ 내지 +150℃의 범위내에서 또는 반응에 사용되는 용매의 비점으로 맞춘다.The reaction temperature is usually set within the range of -20 ° C to + 150 ° C or at the boiling point of the solvent used for the reaction.

반응에 사용되는 물질과 탈수제의 몰비는 자유롭게 결정할 수 있으나, 동물비로 또는 그에 근접한 비로 사용하는 것이 유리하다.The molar ratio of the material used for the reaction and the dehydrating agent can be freely determined, but it is advantageous to use it at or close to the animal ratio.

(i), (ii) 또는 (iii) 경우의 반응이 종결된 후, 반응 혼합물은 유기 용매 추출, 농축 등의 통상적인 후-처리를 거쳐, 본 발명의 목적하는 화합물을 분리할 수 있다. 또한 필요할 경우, 크로마토그래피, 증류 또는 재결정과 같은 통상적인 기술에 의해 정제할 수 있다.After the reaction in case (i), (ii) or (iii) is terminated, the reaction mixture can be subjected to conventional post-treatment such as organic solvent extraction, concentration and the like to separate the desired compound of the present invention. If necessary, it can also be purified by conventional techniques such as chromatography, distillation or recrystallization.

(L이 -NR13-C(=O)-인, 본 발명에 의한 화합물의 제조 공정 G)(Step (G) for preparing a compound according to the present invention, wherein L is -NR 13 -C (= 0)-

이 공정에서는, 하기 화학식(14)의 화합물을 하기 화학식(15)의 화합물과 반응시킨다:In this process, a compound of formula (14) is reacted with a compound of formula (15):

[화학식 14][Formula 14]

[식중 R2, R3, R4, R5, R6, R7, X, Y, Z, V, m 및 n은 각각 상기 정의와 같다][Wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , X, Y, Z, V, m and n are the same as defined above]

[화학식 15][Formula 15]

R1-NH-R13또는 R20-HR 1 -NH-R 13 or R 20 -H

[식중, R1및 R13은 각각 상기 정의와 같고, R20-H는 NH 부분을 함유하는 (R16)s로 치환될 수도 있는 5- 또는 6-원 복소환기이거나; 1종 이상의 산소, 황 또는 질소 원자를 함유하고 있으며, NH부분(예, 피롤, 피페리딘, 2,6-디히드로피롤, 모르폴린)을 함유하는 (R16)s[식중, (R16)s는 상기 정의와 같다]로 치환될 수도 있는 5- 또는 6-원환기이다].[Wherein R 1 and R 13 are each as defined above and R 20 -H is a 5- or 6-membered heterocyclic group which may be substituted with (R 16 ) s containing an NH moiety; (R 16 ) s containing one or more oxygen, sulfur or nitrogen atoms and containing an NH moiety (eg pyrrole, piperidine, 2,6-dihydropyrrole, morpholine), wherein (R 16 s is the same as the above definition] is a 5- or 6-membered cyclic group which may be substituted.

(i) 화학식(14)의 V가 염소, 브롬 또는 1-이미다졸릴일 경우, 사용될 수 있는 용매의 예로는 에테르, 예컨대 디에틸 에테르, 테트라히드로푸란, 디옥산 등; 방향족 탄화수소, 예컨대 벤젠, 톨루엔, 크실렌, 클로로벤젠, 피리딘 등; 탄화수소, 예컨대 n-헥산, n-헵탄, 시클로헥산 등; 할로겐화된 탄화수소, 예컨대 메틸렌 클로라이드, 클로로포름, 사염화 탄소, 1,2-디클로로에탄 등; 에스테르, 예컨대 에틸 아세테이트, 메틸 아세테이트 등; 물; 니트릴, 예컨대 아세토니트릴; 극성 용매, 예컨대 N,N-디메틸포름아미드, N,N-디메틸아세트아미드, N-메틸피롤리돈, 디메틸술폭시드 등; 및 그의 혼합물이 있다.(i) When V in formula (14) is chlorine, bromine or 1-imidazolyl, examples of solvents that may be used include ethers such as diethyl ether, tetrahydrofuran, dioxane and the like; Aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, pyridine and the like; Hydrocarbons such as n-hexane, n-heptane, cyclohexane and the like; Halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane and the like; Esters such as ethyl acetate, methyl acetate and the like; water; Nitriles such as acetonitrile; Polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide and the like; And mixtures thereof.

반응 온도는 통상 -20℃ 내지 +150℃의 범위 또는 반응에 사용되는 용매의 비점으로 맞추며, 바람직하게는 0℃ 내지 50℃로 맞춘다.The reaction temperature is usually set in the range of -20 ° C to + 150 ° C or the boiling point of the solvent used in the reaction, and preferably at 0 ° C to 50 ° C.

반응은 통상적으로, 화학식(14)의 화합물 1몰 당 1 내지 10몰의 몰비의 염기, 예컨대 수산화 나트륨, 수산화 칼륨, 탄산 나트륨, 탄산 칼륨, 트리에틸아민 또는 피리딘의 존재하에서 바람직하게 진행된다.The reaction usually proceeds preferably in the presence of a molar ratio of 1 to 10 moles of base per mole of the compound of formula (14), such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine or pyridine.

용매로서 물을 사용하여 2상 반응을 수행하는 경우, 테트라-n-부틸암모늄브로마이드 또는 벤질트리에틸암모늄 클로라이드 등의 상전이 촉매를 사용하여 반응 속도를 증가시킬 수 있다.When the two-phase reaction is carried out using water as the solvent, a phase transfer catalyst such as tetra-n-butylammonium bromide or benzyltriethylammonium chloride can be used to increase the reaction rate.

(ii) 화학식(14)의 V가 히드록실, 메톡시, 에톡시 또는 프로폭시일 경우, 반응은 통상 용매 없이, 또는 N,N-디메틸포름아미드, N,N-디메틸아세트아미드, N-메틸피롤리돈, 디메틸술폭시드 등의 극성 용매, 혹은 벤젠, 톨루엔, 크실렌, 클로로벤젠 등의 방향족 탄화수소 용매중에서, 50℃ 내지 250℃의 반응 온도로 진행된다.(ii) when V of formula (14) is hydroxyl, methoxy, ethoxy or propoxy, the reaction is usually without solvent or with N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl In polar solvents, such as pyrrolidone and dimethyl sulfoxide, or aromatic hydrocarbon solvents, such as benzene, toluene, xylene, and chlorobenzene, it advances to reaction temperature of 50 degreeC-250 degreeC.

필요할 경우, 반응 촉매로서, 황산, 벤젠술폰산, p-톨루엔술폰산, 활성 실리카겔 등의 산성 물질, 또는 피리딘, 트리에틸아민, 소듐 메톡시드, 소듐 에톡시드, 활성 알루미나 등의 염기성 물질이 화학식(14)의 카르복실산 화합물의 중량에 대해 0.0001 내지 1배의 중량비로 사용될 수 있다.If necessary, as a reaction catalyst, an acidic substance such as sulfuric acid, benzenesulfonic acid, p-toluenesulfonic acid, activated silica gel, or a basic substance such as pyridine, triethylamine, sodium methoxide, sodium ethoxide, activated alumina, etc. It may be used in a weight ratio of 0.0001 to 1 times the weight of the carboxylic acid compound of.

반응에 사용되는 물질과 탈수제의 몰비는 자유롭게 결정할 수 있으나, 동물비로 또는 그에 근접한 비로 사용하는 것이 유리하다.The molar ratio of the material used for the reaction and the dehydrating agent can be freely determined, but it is advantageous to use it at or close to the animal ratio.

(iii) 화학식(14)의 V가 히드록실일 경우, 하기의 제조 공정이 사용될 수 있다.(iii) When V in formula (14) is hydroxyl, the following preparation process can be used.

즉, 화학식(14)의 화합물을 통상 불활성 용매의 존재하에 또는 용매 없이 화학식(15)의 화합물과 반응시켜, 탈수 축합에 의해 목적하는 본 발명의 화합물을 수득한다. 탈수제의 예로는 카르보디이미드, 예컨대 디시클로헥실카르보디이미드 및 1-에틸-3-(3-디메틸아미노프로필)카르보디이미드; 및 무기 탈수제, 예컨대 사염화 규소가 있다. 불활성 용매의 예로는 비-방향족 탄화수소, 예컨대 n-펜탄, n-헥산, n-헵탄, 시클로헥산 등; 방향족 탄화수소, 예컨대 벤젠, 톨루엔, 크실렌, 클로로벤젠, 피리딘, O-디클로로벤젠 등; 염소화된 탄화수소, 예컨대 메틸렌 클로라이드, 클로로포름, 사염화 탄소, 1,2-디클로로에탄 등; 에스테르, 예컨대 에틸 아세테이트, 메틸 아세테이트 등; 아미드, 예컨대 N,N-디메틸포름아미드, N,N-디메틸아세트아미드, N-메틸피롤리돈 등; 니트릴, 예컨대 아세토니트릴; 및 에테르, 예컨대 디에틸 에테르, 테트라히드로푸란, 디옥산 등이 있다.That is, the compound of formula (14) is usually reacted with the compound of formula (15) in the presence or absence of an inert solvent to give the desired compound of the present invention by dehydration condensation. Examples of dehydrating agents include carbodiimides such as dicyclohexylcarbodiimide and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide; And inorganic dehydrating agents such as silicon tetrachloride. Examples of inert solvents include non-aromatic hydrocarbons such as n-pentane, n-hexane, n-heptane, cyclohexane and the like; Aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, pyridine, O-dichlorobenzene and the like; Chlorinated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane and the like; Esters such as ethyl acetate, methyl acetate and the like; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and the like; Nitriles such as acetonitrile; And ethers such as diethyl ether, tetrahydrofuran, dioxane and the like.

반응 온도는 통상 -20℃ 내지 +150℃의 범위내에서 또는 반응에 사용되는 용매의 비점으로 맞춘다.The reaction temperature is usually set within the range of -20 ° C to + 150 ° C or at the boiling point of the solvent used for the reaction.

반응에 사용되는 물질과 탈수제의 몰비는 자유롭게 결정할 수 있으나, 동물비로 또는 그에 근접한 비로 사용하는 것이 유리하다.The molar ratio of the material used for the reaction and the dehydrating agent can be freely determined, but it is advantageous to use it at or close to the animal ratio.

(i), (ii) 또는 (iii) 경우의 반응이 종결된 후, 반응 혼합물은 유기 용매 추출, 농축 등의 통상적인 후-처리를 거쳐, 본 발명의 목적하는 화합물을 분리할 수 있다. 또한 필요할 경우, 크로마토그래피, 증류 또는 재결정과 같은 통상적인 기술에 의해 정제할 수 있다.After the reaction in case (i), (ii) or (iii) is terminated, the reaction mixture can be subjected to conventional post-treatment such as organic solvent extraction, concentration and the like to separate the desired compound of the present invention. If necessary, it can also be purified by conventional techniques such as chromatography, distillation or recrystallization.

(L이 -C(=S)NR13- 또는 -NR13-C(=S)-인, 본 발명에 의한 화합물의 제조 공정 H)(Step H of preparing a compound according to the invention wherein L is -C (= S) NR 13 -or -NR 13 -C (= S)-)

이 공정에서는, L이 -C(=O)NR13- 또는 -NR13-C(=O)-인 본 발명에 의한 화합물을 오황화 인 또는 로웨슨 시약(Lawesson's Reagent)과 반응시킨다.In this process, the compound according to the invention, wherein L is -C (= 0) NR 13 -or -NR 13 -C (= 0)-, is reacted with phosphorus sulphide or Lawesson's Reagent.

사용될 수 있는 용매의 예로는 방향족 탄화수소, 예컨대 벤젠, 톨루엔, 크실렌, 클로로벤젠, 피리딘, 퀴놀린 등이 있다. 필요할 경우, 상기의 용매의 혼합물이 사용될 수 있다.Examples of solvents that can be used are aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, pyridine, quinoline and the like. If necessary, mixtures of the above solvents may be used.

반응 온도는 통상 0℃ 내지 150℃의 범위 또는 반응에 사용되는 용매의 비점으로 맞추며, 바람직하게는 20℃ 내지 150℃ 또는 사용되는 용매의 비점으로 맞춘다.The reaction temperature is usually set in the range of 0 ° C to 150 ° C or the boiling point of the solvent used for the reaction, preferably 20 ° C to 150 ° C or the boiling point of the solvent used.

반응에 사용되는 출발 물질의 몰비는 자유롭게 결정할 수 있으나, 오황화 인 또는 로웨슨 시약은, L이 -C(=O)NR13- 또는 -NR13-C(=O)-인 본 발명에 의한 화합물 1몰당 각각 0.2 내지 20몰 또는 0.5 내지 50몰의 비율로 사용하는 것이 바람직하다.The molar ratio of the starting material used in the reaction can be freely determined, but the phosphorus pentasulphide or Lawesson reagent is according to the invention wherein L is -C (= 0) NR 13 -or -NR 13 -C (= 0)-. It is preferable to use in the ratio of 0.2-20 mol or 0.5-50 mol, respectively per mol of compounds.

(L이 -SO2-NR13-인, 본 발명에 의한 화합물의 제조 공정 I)(Process for preparing a compound according to the invention wherein L is -SO 2 -NR 13- )

이 공정에서는, 화학식(12)의 아민 화합물을 하기 화학식(16)의 술폰산 화합물과 반응시킨다:In this process, the amine compound of formula (12) is reacted with a sulfonic acid compound of formula (16):

[화학식 16][Formula 16]

R1-SO2-L3 R 1 -SO 2 -L 3

[식중, R1은 상기 정의와 같고, L3은 염소 또는 브롬이다].Wherein R 1 is as defined above and L 3 is chlorine or bromine.

사용될 수 있는 용매의 예로는 에테르, 예컨대 디에틸 에테르, 테트라히드로푸란, 디옥산 등; 방향족 탄화수소, 예컨대 벤젠, 톨루엔, 크실렌, 클로로벤젠, 피리딘 등; 탄화수소, 예컨대 n-헥산, n-헵탄, 시클로헥산 등; 할로겐화된 탄화수소, 예컨대 메틸렌 클로라이드, 클로로포름, 사염화 탄소, 1,2-디클로로에탄 등; 에스테르, 예컨대 에틸 아세테이트, 메틸 아세테이트 등; 물; 니트릴, 예컨대 아세토니트릴; 극성 용매, 예컨대 N,N-디메틸포름아미드, N,N-디메틸아세트아미드, N-메틸피롤리돈, 디메틸술폭시드 등; 및 그의 혼합물이 있다.Examples of solvents that can be used include ethers such as diethyl ether, tetrahydrofuran, dioxane and the like; Aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, pyridine and the like; Hydrocarbons such as n-hexane, n-heptane, cyclohexane and the like; Halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane and the like; Esters such as ethyl acetate, methyl acetate and the like; water; Nitriles such as acetonitrile; Polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide and the like; And mixtures thereof.

반응 온도는 통상 -20℃ 내지 +150℃의 범위 또는 반응에 사용되는 용매의 비점으로 맞추며, 바람직하게는 0℃ 내지 50℃로 맞춘다.The reaction temperature is usually set in the range of -20 ° C to + 150 ° C or the boiling point of the solvent used in the reaction, and preferably at 0 ° C to 50 ° C.

반응은 통상적으로, 화학식(16)의 화합물 1몰 당 1내지 10몰의 몰비의 염기, 예컨대 수산화 나트륨, 수산화 칼륨, 탄산 나트륨, 탄산 칼륨, 트리에틸아민 또는 피리딘의 존재하에서 바람직하게 진행된다.The reaction usually proceeds preferably in the presence of a molar ratio of 1 to 10 moles of base per mole of the compound of formula (16), such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine or pyridine.

용매로서 물을 사용하여 2상 반응을 수행하는 경우, 테트라-n-부틸암모늄브로마이드 또는 벤질트리에틸암모늄 클로라이드 등의 상전이 촉매를 사용하여 반응 속도를 증가시킬 수 있다.When the two-phase reaction is carried out using water as the solvent, a phase transfer catalyst such as tetra-n-butylammonium bromide or benzyltriethylammonium chloride can be used to increase the reaction rate.

반응이 종결된 후, 반응 혼합물은 유기 용매 추출. 농축 등의 통상적인 후-처리를 거쳐, 본 발명의 목적하는 화합물을 분리할 수 있다. 또한 필요할 경우, 크로마토그래피, 증류 또는 재결정과 같은 통상적인 기술에 의해 정제할 수 있다.After the reaction is complete, the reaction mixture is extracted with organic solvent. Through conventional post-treatment such as concentration, the desired compound of the present invention can be separated. If necessary, it can also be purified by conventional techniques such as chromatography, distillation or recrystallization.

(L이 -NR13-SO2-인 본 발명에 의한 화합물의 제조 공정 J)(Step J for preparing a compound according to the invention wherein L is -NR 13 -SO 2- )

이 공정에서는, 하기 화학식(17)의 술폰산 화합물을 화학식(15)의 화합물과 반응시킨다:In this process, the sulfonic acid compound of formula (17) is reacted with a compound of formula (15):

[화학식 17][Formula 17]

[식중 R2, R3, R4, R5, R6, R7, X, Y, Z, L3, m 및 n은 각각 상기 정의와 같다][Wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , X, Y, Z, L 3 , m and n are the same as defined above]

사용될 수 있는 용매의 예로는 에테르, 예컨대 디에틸 에테르, 테트라히드로푸란, 디옥산 등; 방향족 탄화수소, 예컨대 벤젠, 톨루엔, 크실렌, 클로로벤젠, 피리딘 등; 탄화수소, 예컨대 n-헥산, n-헵탄, 시클로헥산 등; 할로겐화된 탄화수소, 예컨대 메틸렌 클로라이드, 클로로포름, 사염화 탄소, 1,2-디클로로에탄 등; 에스테르, 예컨대 에틸 아세테이트, 메틸 아세테이트 등; 물; 니트릴, 예컨대 아세토니트릴; 극성 용매, 예컨대 N,N-디메틸포름아미드, N,N-디메틸아세트아미드, N-메틸피롤리돈, 디메틸술폭시드 등; 및 그의 혼합물이 있다.Examples of solvents that can be used include ethers such as diethyl ether, tetrahydrofuran, dioxane and the like; Aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, pyridine and the like; Hydrocarbons such as n-hexane, n-heptane, cyclohexane and the like; Halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane and the like; Esters such as ethyl acetate, methyl acetate and the like; water; Nitriles such as acetonitrile; Polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide and the like; And mixtures thereof.

반응 온도는 통상 -20℃ 내지 +150℃의 범위 또는 반응에 사용되는 용매의 비점으로 맞추며, 바람직하게는 0℃ 내지 50℃로 맞춘다.The reaction temperature is usually set in the range of -20 ° C to + 150 ° C or the boiling point of the solvent used in the reaction, and preferably at 0 ° C to 50 ° C.

반응은 통상적으로, 화학식(17)의 화합물 1몰 당 1 내지 10몰의 몰비의 염기, 예컨대 수산화 나트륨, 수산화 칼륨, 탄산 나트륨, 탄산 칼륨, 트리에틸아민 또는 피리딘의 존재하에서 바람직하게 진행된다.The reaction usually proceeds preferably in the presence of a molar ratio of 1 to 10 moles of base per mole of the compound of formula (17), such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine or pyridine.

용매로서 물을 사용하여 2상 반응을 수행하는 경우, 테트라-n-부틸암모늄 브로마이드 또는 벤질트리에틸암모늄 클로라이드 등의 상전이 촉매를 사용하여 반응 속도를 증가시킬 수 있다.When the two-phase reaction is carried out using water as the solvent, a phase transfer catalyst such as tetra-n-butylammonium bromide or benzyltriethylammonium chloride can be used to increase the reaction rate.

반응이 종결된 후, 반응 혼합물은 유기 용매 추출, 농축 등의 통상적인 후-처리를 거쳐, 본 발명의 목적하는 화합물을 분리할 수 있다. 또한 필요할 경우, 크로마토그래피, 증류 또는 재결정과 같은 통상적인 기술에 의해 정제할 수 있다.After the reaction is completed, the reaction mixture can be subjected to conventional post-treatment such as organic solvent extraction, concentration, etc., to separate the desired compound of the present invention. If necessary, it can also be purified by conventional techniques such as chromatography, distillation or recrystallization.

(L이 -NR13-C(=W1)W-인, 본 발명에 의한 화합물의 제조 공정 K)(Process for preparing a compound according to the invention, wherein L is -NR 13 -C (= W 1 ) W-)

(K공정의 제1단계)(Step 1 of K Process)

이 공정에서는, 하기 화학식(18)의 화합물을 하기 화학식(19)의 (티오) 이소시아네이트 화합물과 반응시켜, 하기 화학식(20)의 카르밤산 유도체를 수득한다:In this process, a compound of formula (18) is reacted with a (thio) isocyanate compound of formula (19) to give a carbamic acid derivative of formula (20):

[화학식 18][Formula 18]

[식중 R2, R3, R4, R5, R6, R7, X, Y, Z, m 및 n은 각각 상기 정의와 같다][Wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , X, Y, Z, m and n are the same as defined above]

[화학식 19][Formula 19]

R1-N=C=W1 R 1 -N = C = W 1

[식중, R1및 W1은 각각 상기 정의와 같다][Wherein R 1 and W 1 are the same as defined above]

[화학식 20][Formula 20]

[식중 R1, R2, R3, R4, R5, R6, R7, W, W1, X, Y, Z, m 및 n은 각각 상기 정의와 같다][Wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , W, W 1 , X, Y, Z, m and n are the same as defined above]

반응은, 필요할 경우 적절한 촉매의 존재하에, 그에 영향을 주지 않는 용매중에서 바람직하게 진행된다.The reaction proceeds preferably in a solvent which, if necessary, in the presence of a suitable catalyst, does not affect it.

사용될 수 있는 용매의 예로는 탄화수소, 예컨대 벤젠, 톨루엔 등; 에테르, 예컨대 디에틸 에테르, 테트라히드로푸란, 디옥산 등; 극성 용매, 예컨대 N,N-디메틸포름아미드, 디메틸술폭시드, 헥사메틸인산 등; 할로겐화된 탄화수소, 예컨대 메틸렌 클로라이드, 클로로포름, 1,2-디클로로에탄, 클로로벤젠 등; 아세토니트릴; 및 니트로메탄이 있다. 필요할 경우 그의 용매 혼합물이 사용될 수 있다.Examples of solvents that can be used include hydrocarbons such as benzene, toluene and the like; Ethers such as diethyl ether, tetrahydrofuran, dioxane and the like; Polar solvents such as N, N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric acid and the like; Halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane, chlorobenzene and the like; Acetonitrile; And nitromethane. If desired, a solvent mixture thereof may be used.

사용될 수 있는 촉매의 예로는 트리에틸아민, 피리딘 및 아세트산 나트륨과 같은 유기 염기; 및 염소화 알루미늄, 염화 수소 및 삼플루오르화 붕소-에테르 착물(BF3-(C2H5)2O)과 같은 산이 있다.Examples of catalysts that can be used include organic bases such as triethylamine, pyridine and sodium acetate; And acids such as aluminum chloride, hydrogen chloride and boron trifluoride-ether complexes (BF 3- (C 2 H 5 ) 2 O).

반응 온도는 통상 -20℃ 내지 반응에 사용되는 용매의 비점으로 맞추며, 바람직하게는 -50℃ 내지 반응에 사용되는 용매의 비점으로 맞춘다.The reaction temperature is usually set at the boiling point of the solvent used in the reaction at -20 ° C, preferably at -50 ° C at the boiling point of the solvent used in the reaction.

반응에 사용되는 물질의 몰비는 자유롭게 결정할 수 있으나, 동물비로 또는 그에 근접한 비로 반응시키는 것이 좋다.The molar ratio of the material used in the reaction can be freely determined, but it is preferable to react at or close to the animal ratio.

반응이 종결된 후, 반응 혼합물은 유기 용매 추출, 농축 등의 통상적인 후-처리를 거쳐, 본 발명의 목적하는 화합물(식중, R13은 H임)을 분리할 수 있다. 또한 필요할 경우, 크로마토그래피, 증류 또는 재결정과 같은 통상적인 기술에 의해 정제할 수 있다.After the reaction is completed, the reaction mixture can be subjected to conventional post-treatment such as organic solvent extraction, concentration, etc., to separate the desired compound of the present invention, wherein R 13 is H. If necessary, it can also be purified by conventional techniques such as chromatography, distillation or recrystallization.

(제조 공정 K의 제2단계)(Step 2 of Manufacturing Process K)

이 공정에서는 화학식(20)의 카르밤산 유도체를 하기 화학식(21)의 할로겐화 화합물과 반응시켜, 본 발명의 화합물(식중, R13은 수소는 아님)을 수득한다:In this process, the carbamic acid derivative of formula (20) is reacted with a halogenated compound of formula (21) to obtain a compound of the invention, wherein R 13 is not hydrogen:

[화학식 21][Formula 21]

R13-L4 R 13 -L 4

[식중, R13은 상기 정의와 같고(그러나, 수소는 아님), L4는 할로겐(예, 염소, 브롬, 요오드)이다].Wherein R 13 is as defined above (but not hydrogen) and L 4 is halogen (eg chlorine, bromine, iodine).

반응은 적절한 촉매의 존재하에 그에 영향을 주지 않는 용매중에서 바람직하제 진행된다.The reaction is preferably carried out in a solvent which does not affect the presence of a suitable catalyst.

사용될 수 있는 용매의 예로는 케톤, 예컨대 아세톤, 메틸 에틸 케톤 등; 탄화수소, 예컨대 벤젠, 톨루엔 등; 에테르, 예컨대 디에틸 에테르, 테트라히드로푸란, 디옥산 등; 할로겐화 탄화수소, 예컨대 메틸렌 클로라이드, 클로로포름, 1,2-디클로로에탄, 클로로벤젠 등; 아세토니트릴; 니트로메탄; 및 피리딘이 있다. 필요할 경우, 이들 용매의 혼합물이 사용될 수 있다.Examples of solvents that can be used include ketones such as acetone, methyl ethyl ketone and the like; Hydrocarbons such as benzene, toluene and the like; Ethers such as diethyl ether, tetrahydrofuran, dioxane and the like; Halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane, chlorobenzene and the like; Acetonitrile; Nitromethane; And pyridine. If necessary, mixtures of these solvents may be used.

사용될 수 있는 염기의 예로는 알칼리 금속의 탄산염, 예컨대 탄산 칼륨; 알칼리 금속의 수소화물, 예컨대 수소화 나트륨; 및 유기 염기, 예컨대 소듐 메톡시드, 소듐 에톡시드, 트리에틸아민, 피리딘 등이 있다.Examples of bases that can be used include carbonates of alkali metals such as potassium carbonate; Hydrides of alkali metals such as sodium hydride; And organic bases such as sodium methoxide, sodium ethoxide, triethylamine, pyridine and the like.

반응 온도는 통상 -10℃ 내지 반응에 사용되는 용매의 비점으로 맞춘다.The reaction temperature is usually set at -10 ° C to the boiling point of the solvent used in the reaction.

반응에 사용되는 물질의 몰비는 자유롭게 결정할 수 있으나, 화학식(21)의 할로겐화 화합물과 염기는, 화학식(20)의 카르밤산 유도체 1몰 당 각각 1 내지 2몰 및 0.9 내지 20몰의 비율로 사용하는 것이 바람직하다.The molar ratio of the material used in the reaction can be freely determined, but the halogenated compound and the base of the formula (21) are used in the ratio of 1 to 2 mol and 0.9 to 20 mol per mol of the carbamic acid derivative of the formula (20), respectively. It is preferable.

반응이 종결된 후, 반응 혼합물은 유기 용매 추출, 농축 등의 통상적인 후-처리를 거쳐, 본 발명의 목적하는 화합물을 분리할 수 있다. 또한 필요할 경우, 크로마토그래피, 증류 또는 재결정과 같은 통상적인 기술에 의해 정제할 수 있다.After the reaction is completed, the reaction mixture can be subjected to conventional post-treatment such as organic solvent extraction, concentration, etc., to separate the desired compound of the present invention. If necessary, it can also be purified by conventional techniques such as chromatography, distillation or recrystallization.

(L이 -WC(=W1)-NR13-인, 본 발명에 의한 화합물의 제조 공정 L)(Production process L of compound according to the invention, wherein L is -WC (= W1) -NR13-)

이 공정에서는, 화학식(12)의 아민 화합물을 하기 화학식(22)의 화합물과 반응시킨다:In this process, the amine compound of formula (12) is reacted with a compound of formula (22):

[화학식 22][Formula 22]

R1-W-C(=W1)-L3 R 1 -WC (= W 1 ) -L 3

[식중, R1, W, W1 및 L3는 각각 상기 정의와 같다].Wherein R 1, W, W 1 and L 3 are the same as defined above.

반응은, 필요할 경우 적절한 촉매의 존재하에, 그에 영향을 주지 않는 용매중에서 바람직하게 진행된다.The reaction proceeds preferably in a solvent which, if necessary, in the presence of a suitable catalyst, does not affect it.

사용될 수 있는 염기의 예로는 알칼리 금속의 탄산염, 예컨대 탄산 칼륨; 및 유기 염기, 예컨대 트리에틸아민, 피리딘 등이 있다. 필요할 경우, 암모늄염(예, 벤질트리에틸암모늄 클로라이드)과 같은 촉매가 반응계에 첨가될 수 있다.Examples of bases that can be used include carbonates of alkali metals such as potassium carbonate; And organic bases such as triethylamine, pyridine and the like. If necessary, a catalyst such as ammonium salt (eg benzyltriethylammonium chloride) may be added to the reaction system.

사용될 수 있는 용매의 예로는 케톤, 예컨대 아세톤, 메틸 에틸 케톤 등; 탄화수소, 예컨대 벤젠, 톨루엔 등; 에테르, 예컨대 디에틸 에테르, 테트라히드로푸란, 디옥산 등; 할로겐화 탄화수소, 예컨대 메틸렌 클로라이드, 클로로포름, 1,2-디클로로에탄, 클로로벤젠 등; 아세토니트릴; 및 니트로메탄이 있다. 필요할 경우, 이들 용매의 혼합물이 사용될 수 있다.Examples of solvents that can be used include ketones such as acetone, methyl ethyl ketone and the like; Hydrocarbons such as benzene, toluene and the like; Ethers such as diethyl ether, tetrahydrofuran, dioxane and the like; Halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane, chlorobenzene and the like; Acetonitrile; And nitromethane. If necessary, mixtures of these solvents may be used.

반응 온도는 통상 -20℃ 내지 반응에 사용되는 용매의 비점으로 맞추며, 바람직하게는 -5℃ 내지 반응에 사용되는 용매의 비점으로 맞춘다.The reaction temperature is usually set at the boiling point of the solvent used in the reaction at -20 deg. C, preferably at the boiling point of the solvent used in the reaction at -5 deg.

반응이 종결된 후, 반응 혼합물은 유기 용매 추출, 농축 등의 통상적인 후-처리를 거쳐, 본 발명의 목적하는 화합물을 분리할 수 있다. 또한 필요할 경우, 크로마토그래피, 증류 또는 재결정과 같은 통상적인 기술에 의해 정제할 수 있다.After the reaction is completed, the reaction mixture can be subjected to conventional post-treatment such as organic solvent extraction, concentration, etc., to separate the desired compound of the present invention. If necessary, it can also be purified by conventional techniques such as chromatography, distillation or recrystallization.

(L이 -NR14-C(=W)NR13-인, 본 발명에 의한 화합물의 제조 공정 M)(Production process M of a compound according to the invention, wherein L is -NR 14 -C (= W) NR 13- )

(M공정의 제1단계)(1st step of M process)

이 공정에서는 화학식(12)의 아민 화합물을 화학식(19)의 (티오) 이소시아네이트 화합물과 반응시켜 하기 화학식(23)의 우레아 유도체 화합물을 수득한다:In this process, the amine compound of formula (12) is reacted with the (thio) isocyanate compound of formula (19) to obtain a urea derivative compound of formula (23):

[화학식 23][Formula 23]

[식중 R1, R2, R3, R4, R5, R6, R7, R13, W, X, Y, Z, m 및 n은 각각 상기 정의와 같다][Wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 13 , W, X, Y, Z, m and n are the same as defined above]

사용될 수 있는 용매의 예로는 탄화수소, 예컨대 벤젠, 톨루엔 등; 에테르, 예컨대 디에틸 에테르, 테트라히드로푸란, 디옥산 등; 극성 용매, 예컨대 N,N-디메틸포름아미드, 디메틸술폭시드, 헥사메틸인산 등; 할로겐화된 탄화수소, 예컨대 메틸렌 클로라이드, 클로로포름, 1,2-디클로로에탄, 클로로벤젠 등; 아세토니트릴; 및 니트로메탄이 있다. 필요할 경우 상기 용매의 혼합물이 사용될 수 있다.Examples of solvents that can be used include hydrocarbons such as benzene, toluene and the like; Ethers such as diethyl ether, tetrahydrofuran, dioxane and the like; Polar solvents such as N, N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric acid and the like; Halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane, chlorobenzene and the like; Acetonitrile; And nitromethane. Mixtures of such solvents may be used if desired.

반응 온도는 통상 -20℃ 내지 반응에 사용되는 용매의 비점 사이의 범위로 맞추며, 바람직하게는 -5℃ 내지 반응에 사용되는 용매의 비점으로 맞춘다.The reaction temperature is usually set within the range between -20 ° C and the boiling point of the solvent used in the reaction, preferably from -5 ° C to the boiling point of the solvent used in the reaction.

반응에 사용되는 물질의 몰비는 자유롭게 결정할 수 있으나, 동몰비로 또는 그에 근접한 비로 반응시키는 것이 좋다.The molar ratio of the material used in the reaction can be freely determined, but it is preferable to react at or near the molar ratio.

반응이 종결된 후, 반응 혼합물은 유기 용매 추출, 농축 등의 통상적인 후-처리를 거쳐, 본 발명의 목적하는 화합물(식중, R14는 H임)을 분리할 수 있다.After the reaction is completed, the reaction mixture can be subjected to conventional post-treatment such as organic solvent extraction, concentration, etc., to separate the desired compound of the present invention, wherein R 14 is H.

또한 필요할 경우, 크로마토그래피, 증류 또는 재결정과 같은 통상적인 기술에 의해 정제할 수 있다.If necessary, it can also be purified by conventional techniques such as chromatography, distillation or recrystallization.

(제조 공정 M의 제2단계)(Step 2 of Manufacturing Process M)

이 공정에서는, 화학식(23)의 우레아 유도체를 하기 화학식(24)의 화합물과 반응시켜, 본 발명의 화합물(식중, R14는 수소는 아님)을 수득한다:In this process, the urea derivative of formula (23) is reacted with a compound of formula (24) to give a compound of the invention, wherein R 14 is not hydrogen:

[화학식 24][Formula 24]

R14-L4 R 14 -L 4

[식중, R14및 L4는 상기 정의와 같다].Wherein R 14 and L 4 are as defined above.

반응은 적절한 촉매의 존재하에 그에 영향을 주지 않는 용매중에서 바람직하게 진행된다.The reaction proceeds preferably in a solvent which does not affect the presence of a suitable catalyst.

사용될 수 있는 용매의 예로는 케톤, 예컨대 아세톤, 메틸 에틸 케톤 등; 탄화수소, 예컨대 벤젠, 톨루엔 등; 에테르, 예컨대 디에틸 에테르, 테트라히드로푸란, 디옥산 등; 할로겐화 탄화수소, 예컨대 메틸렌 클로라이드, 클로로포름, 1,2-디클로로에탄, 클로로벤젠 등; 아세토니트릴; 니트로메탄; 및 피리딘이 있다. 필요할 경우, 이들 용매의 혼합물이 사용될 수 있다.Examples of solvents that can be used include ketones such as acetone, methyl ethyl ketone and the like; Hydrocarbons such as benzene, toluene and the like; Ethers such as diethyl ether, tetrahydrofuran, dioxane and the like; Halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane, chlorobenzene and the like; Acetonitrile; Nitromethane; And pyridine. If necessary, mixtures of these solvents may be used.

사용될 수 있는 염기의 예로는 알칼리 금속의 탄산염, 예컨대 탄산 칼륨; 알칼리 금속의 수소화물, 예컨대 수소화 나트륨; 및 유기 염기, 예컨대 소듐 메톡시드, 소듐 에톡시드, 트리에틸아민, 피리딘 등이 있다.Examples of bases that can be used include carbonates of alkali metals such as potassium carbonate; Hydrides of alkali metals such as sodium hydride; And organic bases such as sodium methoxide, sodium ethoxide, triethylamine, pyridine and the like.

반응 온도는 통상 -10℃ 내지 반응에 사용되는 용매의 비점으로 맞춘다.The reaction temperature is usually set at -10 ° C to the boiling point of the solvent used in the reaction.

반응에 사용되는 물질의 몰비는 자유롭게 결정할 수 있으나, 화학식(24)의 화합물 및 염기는, 화학식 (23)의 우레아 유도체 화합물 1몰 당 각각 1 내지 2몰 및 0.9 내지 20몰의 비율로 사용하는 것이 바람직하다.The molar ratio of the material used in the reaction can be freely determined, but the compound of formula (24) and the base may be used in a ratio of 1 to 2 mol and 0.9 to 20 mol per mol of the urea derivative compound of formula (23), respectively. desirable.

반응이 종결된 후, 반응 혼합물은 유기 용매 추출, 농축 등의 통상적인 후-처리를 거쳐, 본 발명의 목적하는 화합물을 분리할 수 있다. 또한 필요할 경우, 크로마토그래피, 증류 또는 재결정과 같은 통상적인 기술에 의해 정제할 수 있다.After the reaction is completed, the reaction mixture can be subjected to conventional post-treatment such as organic solvent extraction, concentration, etc., to separate the desired compound of the present invention. If necessary, it can also be purified by conventional techniques such as chromatography, distillation or recrystallization.

본 발명의 모든 화합물은, 만약 그것이 비대칭 탄소 원자를 가질 경우, 생리활성을 갖는 그의 광학 활성 이성질체(즉, (+) 형과 (-)형) 및 그의 혼합물을 어떠한 비율로라도 함유하고 있는 것으로 해석된다. 본 발명의 모든 화합물은, 만약 그것이 기하 이성질 현상을 나타낼 경우, 그의 기하 이성질체(즉, 시스-형과 트랜스-형) 및 그의 혼합물을 어떠한 비율로라도 함유하고 있는 것으로 해석된다.All compounds of the present invention are construed to contain, in any proportion, their optically active isomers (ie, (+) and (-) forms) and mixtures thereof that have physiological activity if they have asymmetric carbon atoms. . All compounds of the present invention are interpreted to contain, in any proportion, their geometric isomers (ie, cis- and trans-forms) and mixtures thereof, if they exhibit geometric isomerism.

하기는 본 발명의 화합물의 특정한 실시예이다. 그러나 본 발명은 이 실시예에 한정되지는 않는다.The following are specific examples of the compounds of the present invention. However, the present invention is not limited to this embodiment.

(식중, R1은 표 1 내지 7에 정의한 바와 같다).(Wherein R 1 is as defined in Tables 1 to 7).

[표 1]TABLE 1

[표 2]TABLE 2

[표 3]TABLE 3

[표 4]TABLE 4

[표 5]TABLE 5

[표 6]TABLE 6

[표 7]TABLE 7

(식중, (R12)l은 표 8 내지 21에 정의한 바와 같다).(Wherein (R 12 ) l is as defined in Tables 8 to 21).

[표 8]TABLE 8

[표 9]TABLE 9

[표 10]TABLE 10

[표 11]TABLE 11

[표 12]TABLE 12

[표 13]TABLE 13

[표 14]TABLE 14

[표 15]TABLE 15

[표 16]TABLE 16

[표 17]TABLE 17

[표 18]TABLE 18

[표 19]TABLE 19

[표 20]TABLE 20

[표 21]TABLE 21

(식중, 복소환 고리의 위치 및 (R16)s는 각각 표 22에 정의한 바와 같다).(Wherein the position of the heterocyclic ring and (R 16 ) s are as defined in Table 22, respectively).

[표 22]Table 22

(식중, G, 복소환 고리의 위치 및 (R16)s는 각각 표 23 및 표 24에 정의한 바와 같다).(Wherein G, the position of the heterocyclic ring and (R 16 ) s are as defined in Table 23 and Table 24, respectively).

[표 23]TABLE 23

[표 24]TABLE 24

(식중, G1, G2, 복소환 고리의 위치 및 (R16)s는 각각 표 25에 정의한 바와 같다).(Wherein, G 1 , G 2 , the position of the heterocyclic ring and (R 16 ) s are as defined in Table 25, respectively).

[표 25]TABLE 25

(식중, G1, G2, 복소환 고리의 위치 및 (R16)s는 각각 표 26에 정의한 바와 같다).(Wherein, G 1 , G 2 , the position of the heterocyclic ring and (R 16 ) s are as defined in Table 26, respectively).

[표 26]TABLE 26

[표 27]TABLE 27

[표 28]TABLE 28

[표 29]TABLE 29

[표 30]TABLE 30

[표 31]Table 31

[표 32]Table 32

[표 33]Table 33

[표 34]Table 34

본 발명에 의한 화합물의 제조를 위한 중간체인, 화학식 ( 4) 또는 (5)의 화합물은 예컨대 하기의 반응식 1 내지 4에 따라 제조할 수 있다:Compounds of formula (4) or (5), which are intermediates for the preparation of compounds according to the invention, can be prepared, for example, according to the following schemes 1-4:

[반응식 1]Scheme 1

(식 중, R1, R2, R3, R4, R5, R6, R7, m, n, L2및 L은 각각 상기 정의와 같다)(Wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , m, n, L 2 and L are the same as defined above)

[반응식 2]Scheme 2

*1): JP-A 60-181067/1985* 1): JP-A 60-181067 / 1985

(식 중, R1, R2, R3, R4, R5, R6, R7, m, n, L2및 L은 각각 상기 정의와 같다)(Wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , m, n, L 2 and L are the same as defined above)

[반응식 3]Scheme 3

[반응식 4]Scheme 4

본 발명에 의한 화합물의 제조를 위한 중간체인, 화학식 (6)의 화합물 및 화학식 (7)의 알코올 화합물은 시판 원료로부터 수득할 수 있으며 하기의 반응식 5에 따라 제조할 수 있다:Compounds of formula (6) and alcohol compounds of formula (7), which are intermediates for the preparation of compounds according to the invention, can be obtained from commercial raw materials and can be prepared according to Scheme 5 below:

[반응식 5]Scheme 5

5 (식 중, L6는 메실옥시 또는 토실옥시이고, L3및 X는 각각 상기 정의와 같다)5 (wherein L 6 is mesyloxy or tosyloxy and L 3 and X are as defined above, respectively)

본 발명에 의한 화합물의 제조를 위한 중간체인, 화학식 (8)의 알데히드 화합물은 예컨대 하기의 반응식 6에 따라 제조할 수 있다:Aldehyde compounds of formula (8), which are intermediates for the preparation of compounds according to the invention, can be prepared, for example, according to Scheme 6 below:

[반응식 6]Scheme 6

(식 중, 모든 기호는 각각 상기 정의와 같다)(Wherein all symbols are the same as defined above)

본 발명에 의한 화합물의 제조를 위한 중간체인, 화학식 (9)의 화합물은 예컨대 하기의 반응식 7에 따라 제조할 수 있다:Compounds of formula (9), which are intermediates for the preparation of compounds according to the invention, can be prepared, for example, according to the following scheme 7:

[반응식 7]Scheme 7

본 발명에 의한 화합물의 제조를 위한 중간체인, Y와 Z 모두 산소인 화학식 (18)의 화합물은 예컨대 하기의 반응식 8.1과 8.2에 따라 제조할 수 있다:Compounds of formula (18), in which Y and Z are both oxygen, for the preparation of compounds according to the invention can be prepared, for example, according to the following schemes 8.1 and 8.2:

[반응식 8.1]Scheme 8.1

*5) 예, R.L. Kramer 등, J. Am. Chem. Soc., 43, 880(1921)* 5) Yes, R.L. Kramer et al., J. Am. Chem. Soc., 43, 880 (1921)

*7) 예, L.M. Ellis 등, J. Am. Chem. Soc., 54, 1674(1932)* 7) Yes, L.M. Ellis et al., J. Am. Chem. Soc., 54, 1674 (1932)

*8) 예, 트리페닐포스핀 디에틸 아조디카르복실레이트* 8) eg, triphenylphosphine diethyl azodicarboxylate

(식 중, R2, R3, R4, R5, R6, R7, X, L2, L4, m 및 n은 각각 상기 정의한 바와 같고; L7은 히드록실, 할로겐(예, 염소, 브롬, 요오드), 메실 또는 토실이며; R21은 알코올의 보호기(예, 벤조일)이고; R22는 C1-C4알콕시(예, 메톡시, 에톡시)이다).Wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , X, L 2 , L 4 , m and n are each as defined above; L 7 is hydroxyl, halogen (eg, Chlorine, bromine, iodine), mesyl or tosyl; R 21 is a protecting group of an alcohol (eg benzoyl); R 22 is C 1 -C 4 alkoxy (eg methoxy, ethoxy).

본 발명에 의한 화합물의 제조를 위한 중간체인, 화학식 (3), (12), (14) 또는 (17)의 화합물은 예컨대 하기의 반응식 9.1과 10에 따라 제조할 수 있다:Compounds of formula (3), (12), (14) or (17), which are intermediates for the preparation of the compounds according to the invention, can be prepared according to Schemes 9.1 and 10, for example:

[반응식 9.1]Scheme 9.1

[반응식 9.2]Scheme 9.2

*5) 예, R.L. Kramer et al., J. Am. Chem. Soc., 43, 880(1921)* 5) Yes, R.L. Kramer et al., J. Am. Chem. Soc., 43, 880 (1921)

*6) 예, I.B. Douglass et al., J. Am. Chem. Soc., 60, 1486(1938)* 6) Yes, I.B. Douglass et al., J. Am. Chem. Soc., 60, 1486 (1938)

*7) 예, L.M. Ellis et al., J. Am. Chem. Soc., 54, 1674(1932)* 7) Yes, L.M. Ellis et al., J. Am. Chem. Soc., 54, 1674 (1932)

(식 중, R2, R3, R4, R5, R6, R7, R13, X, Y, Z, L3, L4, m 및 n은 각각 상기 정의한 바와 같고; L5는 메틸, 에틸 또는 프로필이고; L7은 히드록실, 할로겐(예, 염소, 브롬, 요오드), 메실 또는 토실이며; R21은 알코올의 보호기(예, 벤조일)이고; R22는 C1-C4알콕시(예, 메톡시, 에톡시)이다).Wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 13 , X, Y, Z, L 3 , L 4 , m and n are as defined above; L 5 is Methyl, ethyl or propyl; L 7 is hydroxyl, halogen (e.g. chlorine, bromine, iodine), mesyl or tosyl; R 21 is a protecting group of alcohol (e.g. benzoyl); R 22 is C 1 -C 4 Alkoxy (eg methoxy, ethoxy).

[반응식 10]Scheme 10

*9) 예, 트리페닐포스핀 디에틸 아조디카르복실레이트* 9) eg, triphenylphosphine diethyl azodicarboxylate

(식 중, R2, R3, R4, R5, R6, R7, X, Y, m 및 n은 각각 상기 정의한 바와 같다).Wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , X, Y, m and n are as defined above, respectively.

본 발명에 의한 화합물의 제조를 위한 중간체인, 화학식 (13), (15), (16), (19) 또는 (22)의 화합물은 예컨대 하기의 반응식 11과 12에 따라 제조할 수 있다.Compounds of the formulas (13), (15), (16), (19) or (22), which are intermediates for the preparation of the compounds according to the invention, can be prepared according to the following schemes 11 and 12, for example.

[반응식 11]Scheme 11

(식 중, R21은 메톡시, 에톡시, 프로폭시 또는 이미다졸릴이고, 기타 변수는 상기 정의와 같다)Wherein R 21 is methoxy, ethoxy, propoxy or imidazolyl, and other variables are as defined above

[반응식 12]Scheme 12

R1이 벤젠이나 피리딘 고리와 같은 방향족 고리일 경우When R 1 is an aromatic ring such as a benzene or a pyridine ring

본 발명의 화합물은 하기의 예와 같은 여러 종류의 해충이 억제에 매우 효과적이다:The compounds of the present invention are very effective in inhibiting various kinds of pests such as the following examples:

반시목(Hemiptera):Hemiptera:

델파시다에(Delphacidae), 예컨대 라오델팍스 스트리아텔루스(Ladelphaxstriatellus), 니라파르바타 루겐스(Nilaparvata lugens) 및 소가텔라 푸르시페라(Sogatella furcifera); 델토세팔리다에(Deltocephalidae), 예컨대 네포테틱스 신크티셉스(Nephotettix cincticeps) 및 네포테틱스 비레스켄스(Nephotettix virescens); 아피다다에(Aphididae); 알레이로디다에(Aleyrodidae); 콕시다에(Coccidae); 팅기다에(Tingidae); 프실리다에(Rsyllidae) 등.Delphacidae such as Lao delfaxstriatellus, Nilapparvata lugens and Sogatella furcifera; Deltocephalidae such as Nephotettix cincticeps and Nephotettix virescens; Aphididae; Aleyrodidae; Coccidae; Tingidae; Rsyllidae et al.

인시류(Lepidoptera):Leadoptera:

피랄리다에(Pyralidae), 예컨대 칠로 수프레살리스(Chilo suppressalis), 크나팔로크로시스 메디날리스(Cnaphalocrocis medinals), 오스트리니아 누빌라리스(Ostrinia nubilalis), 파라페디아시아 테테렐라(Parapediasia teterrella), 노타르차데가타(Notarcha derogata) 및 플로디아 인테르푼크텔라(Plodia interpunctella); 녹투이다에(Noctuidae), 예컨대 스포돕테라 리투라(Spodoptera litura), 스포돕테라 엑시구아(Spodoptera exigua), 스포돕테라 리토랄리스(Spodoptera littoralis), 슈달레티아 세파라타(Pseudaletia separata), 마메스트라 브라시카에(Mamestra brassicae), 아그로티스 입실론(Agrotis ipsilon), 트리코플루시아 종(Trichoplusia spp.); 헬리오티스 종(Heliothis spp.) 및 헬리코베르파 종(Heliocoverpa spp.); 피에리다에(Pieridae), 예컨대 피에리스 라파에 크루시보라(Pieris rapae crucivora); 토르트리시다에(Tortricidae), 예컨대 아독소피에스 종(Adoxophyes spp.), 그라폴리타 몰레스타(Grapholita molesta) 및 시디아 포모넬라(Cydia pomonella); 카르포사니다에(Carposinidae), 예컨대 카르포사나 니포넨시스(Carposina niponensis); 리오네티다에(Lyonetiidae), 예컨대 리오네티아 종(Lyonetia spp.); 리만트리다에(Lymantridae), 예컨대 리만트리아 종(Lymantria spp.) 및 유프로크티스 종(Euproctis spp.); 포노메우티다에(Yponomeutidae), 예컨대 플루텔라 크실로스텔라(Plutella xylostella); 겔레치다에(Gelechiidae), 예컨대 페크티노포라 고시피엘라(Pectinophora gossypiella); 아크티다에(Arctiide), 예컨대 히판트리아 쿠네아(Hyphantria cunea); 티네이다에(Tineidae), 예컨대 티네아 트란슬루센스(Tinea translucens) 및 티네올라 비셀리엘라(Tineola bisselliella) 등.Pyralidae such as Chilo suppressalis, Cnaphalocrocis medinals, Ostrinia nubilalis, Parapediasia teterrella Notarcha derogata and Plodia interpunctella; Noctuidae such as Spodoptera litura, Spodoptera exigua, Spodoptera littoralis, Pseudaletia separata, Mamestra brassicae, Agrotis ipsilon, Trichoplusia spp .; Heliothis spp. And Heliocoverpa spp .; Pierreidae, such as Pieris rapae crucivora; Tortricidae such as Adoxophyes spp., Grapolita molesta and Cydia pomonella; Carposinidae such as Carposina niponensis; Lyonetidae, such as Lyonetia spp .; Lymantridae, such as Lymantria spp. And Euprotis spp .; Yponomeutidae such as Flutella xylostella; Gelechidae, such as Pectinophora gossypiella; Arctiide, such as Hyphantria cunea; Tinidae, such as Tinea translucens and Tineola bisselliella and the like.

쌍시목(Diptera)Diptera

쿨렉스(Culex), 예컨대 쿨렉스 피피엔스 팔렌스(Culex pallens) 및 쿨레스 트리타에니오르힌쿠스(Cules tritaeniorhynchus); 아에데스(Aedes), 예컨대 아에데스 아에집티(Aedes aegypti) 및 아에데스 알보피크투스(Aedes albopictus); 아노펠레스(Anopheles), 예컨대 아노펠리나에 시넨시스(Anophelinae sinensis); 치로노미다에(Chironomidae); 무스시다에(Muscidae), 예컨대 무스카 도메스티카(Musca domestica) 및 무스시나 스타불란스(Muscina stabulans); 칼리포리다에(Calliphoridae); 사르콥파지다에(Sarcophagidae); 파니아 카니쿨라리스(Fannia canicularis); 안토미다에(Anthomyiidae), 예컨대 델리아 플라투라(Delia Platura) 및 델리아 안티구아(Delia antigua); 트리페티다에(Tripetidae); 드로소필리다에(Drosophilidae); 시코디다에(Psychodidae); 시물리다에(Simuliidae); 타바니다에(Tabanidae); 스토목시나에(Stomoxyinae); 아그로마지다에(Agromyzidae) 등.Culex such as Culex pallens and Cules tritaeniorhynchus; Aedes such as Aedes aegypti and Aedes albopictus; Anopheles such as Anophelinae sinensis; Chironomidae; Muscidae, such as Musca domestica and Muscina stabulans; Calliphoridae; Sarcophagidae; Pania canicularis; Anthomyiidae such as Delia Platura and Delia antigua; Tripetidae; Drosophilidae; Psychodidae; Simuliidae; Tabanidae; Stomoxyinae; Agromyzidae et al.

초시목(Coleoptera):Coleoptera:

디아브로티카(Diabrotica), 예컨대 다아브로티카 비르지페라(Diabrotica virgifera) 및 디아브로티카 운데심푼크타타(Diabrotica undecimpunctata); 스카라바에이다에(Scarabaeidae), 예컨대 아노말라 쿠프레아(Anomala cuprea) 및 아노말라 루포쿠프레아(Anomala rufocuprea); 쿠르쿨리오니다에(Curculionidae), 예컨대 시토필루스 제아마이스(Sitophilus zeamais), 리소폽트루스 오리조필루스(Lissorphoptrus oryphilus), 히페라 파스티카(Hypera pastica) 및 칼로소브루치스 시넨시스(Calosobruchys chinensis); 테네브리오니다에(Tenebrionidae), 예컨대 테네브리오 몰리토르(Tenebrio molitor) 및 트리볼리움 카스타네움(Tribolium castaneum); 크리소멜리다에(Chrysomelidae), 예컨대 아울라코포라 페모랄리스(Aulacophora femoralis), 필로트레타 스트리오라타(Phyllotreta striolata), 아노비다에(Anobiidae) 및 레옵티노타르사 데셈리네아타(Leoptinotarsa decemlineata); 아노비다에(Anobiidae); 에피아크나 종(Epiachna spp.), 예컨대 에피아크나 비진티오크토푼크타타(Epiachna vigintioctopunctata); 리크티다에(Lyctidae); 보스트리치다에(Bostrchidae); 세람비시다에(Cerambycidae); 파에데루스 푸스시페스(Paederus fuscipes) 등.Diabrotica such as Diabrotica virgifera and Diabrotica undecimpunctata; Scarabaeidae such as Anomala cuprea and Anomala rufocuprea; Curculionidae such as Sitophilus zeamais, Lissopphrus oryphilus, Hypera pastica and Calosobruchys chinensis ; Tenebrionidae such as Tenebrio molitor and Tribolium castaneum; Chrysomelidae, such as Aulacophora femoralis, Phylotlotreta striolata, Anobiidae and Leoptinotarsa decemlineata ); Anobiidae; Epiachna spp., Such as Epiachna vigintioctopunctata; Lyctidae; Bostrchidae; Cerambycidae; Paederus fuscipes and the like.

딕티옵테라(Dictyoptera):Dictoptera:

블라텔라 게르마니카(Blattella germanica), 페리플라네타 푸리지노사(Prriplaneta fuliginosa), 페로플라네타 아메리카나(Peroplaneta americana), 페리플라네타 브룬네아(Periplaneta brunnea), 블라타 오리엔탈리스(Blatta orientalis) 등.Blatella germanica, Perriplaneta fuliginosa, Perplanetata americana, Periplaneta brunnea, Blata orientalis.

티사놉테라(Thysanoptera):Thysanoptera:

트립스 팔미(Thrips palmi), 트립스 티바시(Thrips tabaci), 트립스 하와이엔시스(Thrips hawaiiensis) 등.Trips palmi, Trips tabaci, Trips hawaiiensis.

막시목(Hymenoptera):Hymenoptera:

포르미시다에(Formicidae), 비스피다에(Vespidae), 베틸리다에(Bethylidae), 텐트레디니다에(Tenthredinidae), 예컨대 이탈리아 로사에 자포넨시스(Athalia rosae japonensis) 등.Formicidae, Vespidae, Bethylidae, Tenthredinidae, such as Athalia rosae japonensis, etc.

오르톱테라(Orthoptera):Orthoptera:

그릴로탈피다에(Gryllotalpidae), 아크리디다에(Acrididae) 등.Gryllotalpidae, Acrididae, etc.

벼룩목(Siphonaptera):Siphonaptera:

푸렉스 이리탄스(Purex irritans) 등.Purex irritans and the like.

아노플루라(Anoplura):Anoplura:

페디쿨루스 후마누스 카피티스(Pediculus humanus capitis), 프티루스 푸비스(Phthirus pubis) 등.Pediculus humanus capitis, Phthirus pubis, and the like.

이솝테라(Isoptera)(termites):Isoptera (termites):

리티쿨리테메스 스페라투스(Reticulitermes speratus), 콥토테르메스 포르모사누스(Coptotermes formosanus) 등.Reticulitermes speratus, Coptotermes formosanus and the like.

본 발명의 화합물은 또한 통상적인 살충제에 내성을 갖는 여러 종류의 해충의 억제에도 효과적이다.The compounds of the present invention are also effective in inhibiting various types of pests that are resistant to conventional pesticides.

본 발명에 의한 화합물이 살충제의 활성 성분으로서 사용될 경우, 상기물은 기타 어떠한 성분의 첨가도 없이 그대로 사용될 수 있다. 그러나, 본 발명에 의한 화합물은 통상 오일 분무물, 유화성 농축물, 습윤성 분말, 유동상, 과립, 분진, 에어로졸, 훈연제, 독성 미끼 등의 투여 형태로 조제된다. 이러한 투여 형태는 통상 본 발명에 의한 화합물은 고체 담체, 액체 담체, 기체상 담체 또는 미끼와 혼합함으로써, 그리고 필요한 경우 계면활성제 및 기타 조제를 위해 사용되는 보조제를 첨가함으로써 제조한다.When the compound according to the invention is used as the active ingredient of the pesticide, the above water can be used as it is without addition of any other ingredients. However, the compounds according to the invention are usually formulated in dosage forms such as oil sprays, emulsifiable concentrates, wettable powders, fluidized beds, granules, dusts, aerosols, smokers, toxic baits and the like. Such dosage forms are usually prepared by mixing the compounds according to the invention with solid carriers, liquid carriers, gaseous carriers or baits, and by adding adjuvant used for surfactants and other preparations, if necessary.

각각의 투여 형태는 통상적으로 활성 성분으로서 1종 이상의 본 발명에 의한 화합물을 0.01 중량% 내지 95 중량%의 양으로 함유한다.Each dosage form typically contains, as active ingredient, one or more compounds according to the invention in an amount of 0.01% to 95% by weight.

조제를 위해 사용되는 고체 담체의 예로는 고령토, 규조토, 합성 산화 규소 수화물, 벤토나이트, 푸바사미 흙, 산성 흙 등의 흙 물질의 미분말 또는 과립; 견운모, 석영, 황, 활성탄, 탄산 칼슘, 실리카 수화물 등 다양한 종류의 무기 광물, 탈크 및 세라믹; 및 황산 암모늄, 인산 암모늄, 질산 암모늄, 우레아, 염화 암모늄 등의 화학 비료가 있다.Examples of solid carriers used for the preparation include fine powders or granules of soil materials such as kaolin, diatomaceous earth, synthetic silicon oxide hydrate, bentonite, fuvasami soil, acid soil, etc .; Various kinds of inorganic minerals such as mica, quartz, sulfur, activated carbon, calcium carbonate, silica hydrate, talc and ceramics; And chemical fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride and the like.

액체 담체의 예로는 물; 메탄올, 에탄올 등의 알코올; 아세톤, 메틸 에틸 케톤 등의 케톤; 벤진, 톨루엔, 크실렌, 에틸벤젠, 메틸나프탈렌 등의 방향족 탄화수소; 헥산, 시클로헥산, 케로신, 가스 오일 등의 지방족 탄화수소; 에틸 아세테이트, 부틸 아세테이트 등의 에스테르; 아세토니트릴, 이소부티로니트릴 등의 니트릴; 디이소프로필에테르, 디옥산 등의 에테르; N,N-디메틸포름아미드, N,N-디메틸아세트아미드 등의 산 아미드; 디클로로메탄, 트리클로로에탄, 사염화 탄소 등의 할로겐화 탄화수소; 디메틸 술폭시드; 및 콩기름, 면실유 등의 식물성유가 있다.Examples of liquid carriers include water; Alcohols such as methanol and ethanol; Ketones such as acetone and methyl ethyl ketone; Aromatic hydrocarbons such as benzine, toluene, xylene, ethylbenzene and methylnaphthalene; Aliphatic hydrocarbons such as hexane, cyclohexane, kerosene and gas oil; Esters such as ethyl acetate and butyl acetate; Nitriles such as acetonitrile and isobutyronitrile; Ethers such as diisopropyl ether and dioxane; Acid amides such as N, N-dimethylformamide and N, N-dimethylacetamide; Halogenated hydrocarbons such as dichloromethane, trichloroethane and carbon tetrachloride; Dimethyl sulfoxide; And vegetable oils such as soybean oil and cottonseed oil.

기체성 담체 또는 분사체의 예로는 플론(flon) 가스, 부탄 가스, LPG(액화 석유 가스), 디메틸 에테르 및 이산화 탄소가 있다.Examples of gaseous carriers or injectors include flon gas, butane gas, LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide.

계면활성제의 예로는 알킬 술페이트, 알킬 술포네이트, 알킬 아릴술포네이트, 알킬 아릴 에테르 및 그의 폴리옥시에틸렌 유도체, 폴리에틸렌 글리콜 에테르, 다가 알코올 에스테르 및 당 알코올 유도체가 있다.Examples of surfactants include alkyl sulfates, alkyl sulfonates, alkyl arylsulfonates, alkyl aryl ethers and polyoxyethylene derivatives thereof, polyethylene glycol ethers, polyhydric alcohol esters and sugar alcohol derivatives.

조제를 위해 사용되는 보조제, 예컨대 정착제 또는 분산제의 예로는 카제인, 젤라틴, 다당류, 예컨대 녹말, 아라비아 고무, 셀룰로오스 유도체 및 알긴산, 리그닌 유도체, 벤토나이트, 설탕, 및 합성 수용성 중합체, 예컨대 폴리비닐 알코올, 폴리비닐 피릴리돈 및 폴리아크릴산이 있다.Examples of auxiliaries used for the preparation, such as fixatives or dispersants, include casein, gelatin, polysaccharides such as starch, gum arabic, cellulose derivatives and alginic acid, lignin derivatives, bentonite, sugars, and synthetic water soluble polymers such as polyvinyl alcohol, poly Vinyl pyrididone and polyacrylic acid.

안정제의 예로는 PAP(이소프로필 산 포스페이트), BHT(2,6-디-tert-부틸-4-메틸페놀), BHA(2-tert-부틸-4-메톡시페놀과 3-tert-부틸-4-메톡시페놀의 혼합물), 식물성유, 미네랄유, 계면활성제, 지방산 및 그의 에스테르가 있다.Examples of stabilizers include PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert-butyl-4-methoxyphenol and 3-tert-butyl- Mixtures of 4-methoxyphenol), vegetable oils, mineral oils, surfactants, fatty acids and esters thereof.

독성 미끼에 사용되는 기초 물질의 예로는 곡물 분말, 식물성유, 설탕, 결정성 셀룰로오스 등의 미끼 물질; 디부틸히드록시톨루엔, 노르디히드로구아이아레트산 등의 산화 방지제; 디히드로아세트산 등의 보존제; 붉은 고추 분말 등의 잘못된 섭식을 방지하는 물질; 치즈향, 양파향 등의 유인향이 있다.Examples of the base material used for the toxic bait include bait materials such as grain powder, vegetable oil, sugar, crystalline cellulose; Antioxidants such as dibutyl hydroxytoluene and nordihydroguaiaric acid; Preservatives such as dihydroacetic acid; Substances that prevent wrong feeding, such as red pepper powder; There are manned flavors such as cheese flavor and onion flavor.

이렇게 얻어진 투여 형태는 그대로 또는 물에 희석하여 사용한다. 투여형태는 또한 기타 살충제, 살선충제, 살진드기제, 살균제, 살진균제, 제초제, 식물성장 조절제, 상승제(synergists), 비료, 토질 개량제 및/또는 비혼합 조건 또는 프리-믹싱(pre-mixing) 조건하의 동물 먹이와 함께 사용될 수 있다.The dosage forms thus obtained are used as such or diluted in water. Dosage forms also include other insecticides, nematicides, acaricides, fungicides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil improvers and / or non-mixed conditions or pre-mixing. ) Can be used with animal food under conditions.

사용될 수 있는 살충제, 살진드기제 및/또는 살선충제의 예로는 유기인계 화합물, 예컨대 페니트로티온[0,0-디메틸 0-(3-메틸-4-니트로페닐)포스포로티오에이트], 펜틴[0,0-디메틸 0-(3-메틸-4-메틸티오페닐)포스포로티오에이트], 디아지논[0,0-디에틸 0-2-이소프로필-6-메틸피리미딘-4-일-포스포로티오에이트], 클로르피리포스[0,0-디에틸 0-3,5,6-트리클로로-2-피리딜포스포로티오에이트], 아세페이트[0,S-디메틸아세틸포스포르아미도티오에이트], 메티다티온[S-2,3-디히드로-5-메톡시-2-옥소-1,3,4-티아디아졸-3-일메틸 0,0-디에틸포스포로디티오에이트], 디술포톤[0,0-디에틸 S-2-에틸티오에틸포스포로티오에이트], DDVP[2,2-디클로로비닐디메틸포스페이트], 술프로포스[0-에틸 0-4-(메틸티오)페닐 S-프로필 포스포로디티오에이트], 시아노포스[0-4-시아노페닐 0,0-디메틸포스포로티오에이트], 디옥사벤조포스[2-메톡시-4H-1,2,3-벤조디옥사포스피닌-2-술피드], 디메토에이트[0,0-디메틸-S-(N-메틸카르바모일메틸)디티오포스페이트], 펜토에이트[에틸 2-디메톡시포스피노티오일티오(페닐)아세테이트], 말라티온[디에틸(디메톡시포스피노티오일티오)숙시네이트], 트리클로르폰[디메틸 2,2,2-트리클로로-1-히드록시에틸포스포네이트], 아진포스-메틸[S-3,4-디히드로-4-옥소-1,2,3-벤조트리아진-3-일메틸 0,0-디메틸포스포로디티오에이트], 모노크로토포스[디메틸 (E)-1-메틸-2-(메틸카르바모일)비닐포스페이트], 에티온[0,0,0',0'-테트라에틸 S,S'-메틸렌비스(포스포로디티오에이트)] 및 프로페노포스[0-4-브로모-2-클로로페닐 0-에틸 S-프로필 포스포로티오에이트]; 카르바메이트 화합물, 예컨대 BMPC[2-sec-부틸페닐메틸카르바메이트], 벤푸라카르브[에틸 N-[2,3-디히드로-2,2-디메틸벤조푸란-7-일옥시카르보닐(메틸)아미노티오-N-이소프로필-β-알라니네이트], 프로폭수르[2-이소프로폭시페닐 N-메틸카르바메이트], 카르보술판[2,3-디히드로-2,2-디메틸-7-벤조[b]푸라닐 N-디부틸아미노티오-N-메틸카르바메이트], 카르바릴[1-나프틸-N-메틸카르바메이트], 메토밀[S-메틸-N-(메틸카르바모일)옥시]티오아세트이미데이트, 에티오펜카르브[2-(에틸티오메틸)페닐메티카르바메이트], 알디카르브[2-메틸-2-(메틸티오)프로판알데히드-0-메틸카르바모일옥심], 옥사밀[N,N-디메틸-2-메틸카르바모일옥시이미노-2-(메틸티오)아세트아미드], 페노티오카르브[S-(4-페녹시부틸)-N,N-디메틸티오카르바메이트], 티오디카르브[3,7,9,13-테트라메틸-5,11-디옥사-2,8,14-트리티아-4,7,9,12-테트라아자펜타데카-3,12-디엔-6,10-디온] 및 알라닐카르브[에틸 (Z)-N-벤질-N-{[메틸(1-메틸티오에틸렌아미노옥시카르보닐)아미노]티오}-β-알라니네이트]; 피레트로이드 화합물, 예컨대 에토펜프로스[2-(4-에톡시페닐)-2-메틸프로필-3-페녹시벤질에테르], 펜발레레이트[(RS)-α-시아노-3-페녹시벤질 (RS)-2-(4-클로로페닐)-3-메틸부티레이트], 에스펜발레레이트[(S)-α-시아노-3-페녹시벤질 (S)-2-(4-클로로페닐)-3-메틸부티레이트], 펜프로파트린[(RS)-α-시아노-3-페녹시벤질-2,2,3,3-테트라메틸시클로프로판카르복실레이트], 시페메트린[(RS)-α-시아노-3-페녹시벤질 (1RS,3RS)-3-(2,2-디클로로비닐)-2,2-디메틸시클로프로판카르복실레이트], 페메트린[3-페녹시벤질 (1RS,3RS)-3-(2,2-디클로로비닐)-2,2-디메틸시클로프로판카르복실레이트], 시할로트린[(RS)-α-시아노-3-페녹시벤질 (Z)-(1RS)-시스-3-(2-클로로-3,3,3-트리플루오로프로프-1-에닐)-2,2-디메틸시클로프로판카르복실레이트], 델타메트린[(S)-α-시아노-m-페녹시벤질 (1R,3R)-3-(2,2-디브로모비닐)-2,2-디메틸시클로프로판카르복실레이트], 시클로프로트린[(RS)-α-시아노-3-페녹시벤질 (RS)-2,2-디클로로-1-(4-에톡시페닐)시클로프로판카르복실레이트], 플루발리네이트[α-시아노-3-페녹시벤질 N-(2-클로로-α,α,α-트리플루오로-p-톨릴)-D-발리네이트], 비펜트린[2-메틸피베닐-3-일-메틸)(Z)-(1RS)-시스-3-(2-클로로-3,3,3-트리플루오로프로프-1-에닐)-2,2-디메틸시클로프로판카르복실레이트], 아크리나트린[(S)-α-시아노-(3-페녹시페닐)메틸[1R-{1α(S*),3α(Z)}]-2,2-디메틸-3-[3-옥소-3-(2,2,2-트리플루오로-1-(트리플루오로메틸)에톡시-1-프로페닐]시클로프로판카르복실레이트], 2-메틸-2-(4-브로모디플루오로메톡시페닐)프로필(3-페녹시벤질)에테르, 트라로메트린[(S)-α-시아노-3-페녹시벤질 (1R,3R)-[(1'RS)-(1',1',2',2'-테트라브로모에틸)]-2,2-디메틸시클로프로판카르복실레이트] 및 실라플루오펜[4-에톡시페닐[3-(4-플루오로-3-페녹시페닐)프로필]디메틸실란]; 티아디아진 유도체, 예컨대 부프로페진[2-tert-부틸이민-3-이소프로필-5-페닐-1,3,5-티아디아진-4-온]; 니트로이미다졸리딘 유도체 예컨대 이미다클로프리드[1-(6-클로로-3-프리딜메틸)-N-니트로이미다졸리딘-2-일리덴아민]; 네레이스톡신 유도체, 예컨대 카르탑[S,S'-(2-디메틸아미노트리메틸렌)비스티오카르바메이트], 티오시클람[N,N-디메틸-1,2,3-트리티안-5-일아민] 및 벤술탑[S,S'-(2-디메틸아미노트리메틸렌 디(벤젠티오술포네이트)]; N-시아노아미딘 유도체, 예컨대 아세트아미프리드[N-시아노-N'-메틸-N'-(6-클로로-3-피리딜메틸)아세트아미딘]; 염소화된 탄화수소 화합물, 예컨대 엔도술판[6,7,8,9,10,10-헥사클로로-1,5,5a,6,9,9a-헥사히드로-6,9-메타노-2,4,3-벤조디옥사티에피녹사이드], γ-BHC [1,2,3,4,5,6-헥사클로로시클로헥산] 및 켈탄[1,1-비스(클로로페닐)-2,2,2-트리클로로에탄올]; 벤조일페닐우레아 화합물, 예컨대 클로르플루아주론[1-(3,5-디클로로-4-(3-클로로-5-트리플루오로메틸피리딘-2-일옥시)페닐)-3-(2,6-디플루오로벤조일)우레아], 테플루벤주론[[1-(3,5-디클로로-2,4-디플루오로페닐)-3-(2,6-디플루오로벤조일)우레아] 및 풀페녹스론[1-(4-(2-클로로-4-트리플루오로메틸페녹시)-2-플루오로페닐)-3-(2,6-디플루오로벤조일)우레아]; 프로마미딘유도체, 예컨대 아미트레즈[N,N'-[(메틸이미노)디메틸리딘]-디-2,4-크실리딘] 및 클로르디메포름[N'-(4-클로로-2-메틸페닐)-N,N-디메틸메탄이미다미드]; 티오우레아유도체, 예컨대 디아펜티우론[N-(2,6-디이소프로필-4-페녹시페닐)-N'-tert-부틸카르보디이미드]; 브로모프로필레이트[이소프로필 4,4'-디브로모벤질레이트], 테트라디폰[4-클로로페닐-2,4,5-트리클로로페닐술폰], 퀴노메티오네이트[S,S-6-메틸퀴녹살린-2,3-디일디티오카르보네이트], 프로파기트[2-(4-tert-부틸페녹시)시클로헥실프로프-2-일 술파이트], 펜부타틴 옥시드[비스[트리스(2-메틸-2-페닐프로필)틴]옥사이드], 헥시타아족스[(4RS, 5RS)-5-(4-클로로페닐)-N-클로로헥실-4-메틸-2-옥소-1,3-티아졸리딘-3-카르복사미드], 클로펜테진[3,6-비스(2-클로로페닐)-1,2,4,5-테트라진], 피리다벤[2-tert-부틸-5-(4-tert-부틸벤질티오)4-클로로피리다진-3(2H)-온], 펜피록시메이트(tert-부틸 (E)-4-[(1,3-디메틸-5-페녹시피라졸-4-일)메틸렌아미노옥시메틸]벤조에이트], 테브펜피라드[N-(4-tert-부틸벤질)-4-클로로-3-에틸-1-메틸-5-피라졸레카르복시아미드], 테트라나크틴을 포함하는 폴리나크틴 착물, 디나크틴 및 트리나크틴; 미베메크틴, 아베메크틴, 이베메크틴, 아자디라크틴[AZAD], 피리미디펜[5-클로로-N-[2-{4-(2-에톡시에틸)-2,3-디메틸페녹시}에틸]-6-에틸피리미딘-4-아민], 클로로페나필[4-브로모-2-(4-클로로페닐)-1-에톡시메틸-5-트리플루오로메틸피롤-3-카르보니트릴], 테브페노지드[N-tert-부틸-N'-(4-에틸벤조일)-3,5-디메틸벤조히드라지드], 피프로닐[5-아미노-1-(2,6-디클로로-α,α,α-트리플루오로-p-톨릴)-4-트리플루오로메틸술피닐피라졸-3-카르보니트라이트] 및 피메트로진[2,3,4,5-테트라히드로-3-옥소-4-[(피리딘-3-일)-메틸렌아미노]-6-메틸-1,2,4-트리아진]이 있다.Examples of pesticides, mites and / or nematicides which may be used are organophosphorus compounds such as phenythrothione [0,0-dimethyl 0- (3-methyl-4-nitrophenyl) phosphothioate], fentin [0,0-dimethyl 0- (3-methyl-4-methylthiophenyl) phosphothioate], diazinone [0,0-diethyl 0-2-isopropyl-6-methylpyrimidin-4-yl -Phosphothioate], chlorpyriphos [0,0-diethyl 0-3,5,6-trichloro-2-pyridylphosphorothioate], acetate [0, S-dimethylacetylphosphorami Dothioate], methidathione [S-2,3-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3-ylmethyl 0,0-diethylphosphorodiity Oate], disulfon [0,0-diethyl S-2-ethylthioethylphosphorothioate], DDVP [2,2-dichlorovinyldimethylphosphate], sulfpropos [0-ethyl 0-4- ( Methylthio) phenyl S-propyl phosphorodithioate], cyanophosph [0-4-cyanophenyl 0,0-dimethylphospho Rothioate], dioxabenzophosph [2-methoxy-4H-1,2,3-benzodioxaphosphinine-2-sulfide], dimethoate [0,0-dimethyl-S- (N- Methylcarbamoylmethyl) dithiophosphate], pentoate [ethyl 2-dimethoxyphosphinothioylthio (phenyl) acetate], malathion [diethyl (dimethoxyphosphinothioylthio) succinate], trichlor Phon [dimethyl 2,2,2-trichloro-1-hydroxyethylphosphonate], azine force-methyl [S-3,4-dihydro-4-oxo-1,2,3-benzotriazine- 3-ylmethyl 0,0-dimethylphosphorodithioate], monocrotophosph [dimethyl (E) -1-methyl-2- (methylcarbamoyl) vinylphosphate], ethion [0,0,0 ' , 0'-tetraethyl S, S'-methylenebis (phosphorodithioate)] and propenophosph [0-4-bromo-2-chlorophenyl 0-ethyl S-propyl phosphorothioate]; Carbamate compounds such as BMPC [2-sec-butylphenylmethylcarbamate], benfuracarb [ethyl N- [2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl (Methyl) aminothio-N-isopropyl-β-alanineate], propoxur [2-isopropoxyphenyl N-methylcarbamate], carbosulfan [2,3-dihydro-2,2 -Dimethyl-7-benzo [b] furanyl N-dibutylaminothio-N-methylcarbamate], carbaryl [1-naphthyl-N-methylcarbamate], methyl [S-methyl-N -(Methylcarbamoyl) oxy] thioacetimate, thiophencarb [2- (ethylthiomethyl) phenylmethiccarbamate], aldicarb [2-methyl-2- (methylthio) propanealdehyde- 0-methylcarbamoyl oxime], oxamyl [N, N-dimethyl-2-methylcarbamoyloxyimino-2- (methylthio) acetamide], phenothiocarb [S- (4-phenoxybutyl ) -N, N-dimethylthiocarbamate], thiodicarb [3,7,9,13-tetramethyl-5,11-dioxa-2 , 8,14-trithia-4,7,9,12-tetraazapentadeca-3,12-diene-6,10-dione and alanylcarb [ethyl (Z) -N-benzyl-N- {[Methyl (1-methylthioethyleneaminooxycarbonyl) amino] thio} -β-alanineate]; Pyrethroid compounds such as etofenproth [2- (4-ethoxyphenyl) -2-methylpropyl-3-phenoxybenzylether], fenvallate [(RS) -α-cyano-3-phenoxybenzyl (RS) -2- (4-chlorophenyl) -3-methylbutyrate], esfen valerate [(S) -α-cyano-3-phenoxybenzyl (S) -2- (4-chlorophenyl) -3-methylbutyrate], phenpropatrine [(RS) -α-cyano-3-phenoxybenzyl-2,2,3,3-tetramethylcyclopropanecarboxylate], cifemethrin [(RS ) -α-cyano-3-phenoxybenzyl (1RS, 3RS) -3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate], pemetrin [3-phenoxybenzyl ( 1RS, 3RS) -3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate], sihalothrin [(RS) -α-cyano-3-phenoxybenzyl (Z) -(1RS) -cis-3- (2-chloro-3,3,3-trifluoroprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate], deltamethrin [(S)- α-cyano-m-phenoxybenzyl (1R, 3R) -3- (2,2-dibromoby ) -2,2-dimethylcyclopropanecarboxylate], cycloprotrin [(RS) -α-cyano-3-phenoxybenzyl (RS) -2,2-dichloro-1- (4-ethoxyphenyl ) Cyclopropanecarboxylate], fluvalinate [α-cyano-3-phenoxybenzyl N- (2-chloro-α, α, α-trifluoro-p-tolyl) -D-valinate], Bifenthrin [2-methylfibenyl-3-yl-methyl) (Z)-(1RS) -cis-3- (2-chloro-3,3,3-trifluoroprop-1-enyl) -2 , 2-dimethylcyclopropanecarboxylate], acrinatrin [(S) -α-cyano- (3-phenoxyphenyl) methyl [1R- {1α (S *), 3α (Z)}]-2 , 2-dimethyl-3- [3-oxo-3- (2,2,2-trifluoro-1- (trifluoromethyl) ethoxy-1-propenyl] cyclopropanecarboxylate], 2- Methyl-2- (4-bromodifluoromethoxyphenyl) propyl (3-phenoxybenzyl) ether, traromethrin [(S) -α-cyano-3-phenoxybenzyl (1R, 3R)-[( 1'RS)-(1 ', 1', 2 ', 2'-tetrabromoethyl)]-2,2-dimethylcyclopropanecarboxylate] and seal Fluorene-thiophene [4-ethoxyphenyl [3- (4-fluoro-3-phenoxyphenyl) propyl] dimethylsilane in; Thiadiazine derivatives such as buprofezin [2-tert-butylimine-3-isopropyl-5-phenyl-1,3,5-thiadiazin-4-one]; Nitroimidazolidine derivatives such as imidacloprid [1- (6-chloro-3-pridylmethyl) -N-nitroimidazolidine-2-ylideneamine]; Neracetoxin derivatives such as cartope [S, S '-(2-dimethylaminotrimethylene) bisthiocarbamate], thiocyclam [N, N-dimethyl-1,2,3-trithiane-5- Ylamine] and bensultopes [S, S '-(2-dimethylaminotrimethylene di (benzenethiosulfonate)]; N-cyanoamidine derivatives such as acetamiprid [N-cyano-N'-methyl- N '-(6-chloro-3-pyridylmethyl) acetamidine] chlorinated hydrocarbon compounds, such as endosulfan [6,7,8,9,10,10-hexachloro-1,5,5a, 6 , 9,9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepinoside], γ-BHC [1,2,3,4,5,6-hexachlorocyclohexane] And Keltan [1,1-bis (chlorophenyl) -2,2,2-trichloroethanol] Benzoylphenylurea compounds such as chlorfluazuron [1- (3,5-dichloro-4- (3-chloro -5-trifluoromethylpyridin-2-yloxy) phenyl) -3- (2,6-difluorobenzoyl) urea], teflubenzuron [[1- (3,5-dichloro-2,4 -Difluorophenyl) -3- (2,6-difluorobenzoyl) urea] and fulphenoxrone [1- (4- (2-chloro-4-trifluoromethylphenoxy) -2-fluorophenyl) -3- (2,6 -Difluorobenzoyl) urea], a promamidine derivative such as amitrez [N, N '-[(methylimino) dimethylidine] -di-2,4-xyldine] and chlordimeform [N '-(4-chloro-2-methylphenyl) -N, N-dimethylmethaneimidamid]; thiourea derivatives such as diafenthiuron [N- (2,6-diisopropyl-4-phenoxyphenyl)- N'-tert-butylcarbodiimide], bromopropylate [isopropyl 4,4'-dibromobenzylate], tetradipon [4-chlorophenyl-2,4,5-trichlorophenylsulphone], Quinomethionate [S, S-6-methylquinoxaline-2,3-diyldithiocarbonate], propargite [2- (4-tert-butylphenoxy) cyclohexylprop-2-ylsulphate Fight], fenbutatin oxide [bis [tris (2-methyl-2-phenylpropyl) tin] oxide], hexitaxox [(4RS, 5RS) -5- (4-chlorophenyl) -N-cle Lohexyl-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide], clofentezin [3,6-bis (2-chlorophenyl) -1,2,4,5- Tetrazine], Pyridaben [2-tert-butyl-5- (4-tert-butylbenzylthio) 4-chloropyridazin-3 (2H) -one], Phenpyroximate (tert-butyl (E) -4 -[(1,3-dimethyl-5-phenoxypyrazol-4-yl) methyleneaminooxymethyl] benzoate], tevfenpyrad [N- (4-tert-butylbenzyl) -4-chloro-3- Ethyl-1-methyl-5-pyrazolecarboxyamide], polynactin complexes including tetranactin, dinactin and trinactin; Mibemethin, Abemethin, Ivemethin, Azadirachtin [AZAD], Pyrimidiphen [5-chloro-N- [2- {4- (2-ethoxyethyl) -2,3-dimethylphenoxy Ethyl} -6-ethylpyrimidin-4-amine], chlorophenafil [4-bromo-2- (4-chlorophenyl) -1-ethoxymethyl-5-trifluoromethylpyrrole-3- Carbonitrile], teffenozide [N-tert-butyl-N '-(4-ethylbenzoyl) -3,5-dimethylbenzohydrazide], fipronil [5-amino-1- (2,6- Dichloro-α, α, α-trifluoro-p-tolyl) -4-trifluoromethylsulfinylpyrazole-3-carbonitrite] and pymetrozine [2,3,4,5-tetrahydro- 3-oxo-4-[(pyridin-3-yl) -methyleneamino] -6-methyl-1,2,4-triazine].

본 발명에 의한 화합물이 농업용 살충제의 활성 성분으로서 사용될 경우, 그의 적용량은 통상 10 에이커 당 0.1 내지 100g의 범위이다. 물로 희석한 후 사용하는 유화성 농축물, 습윤성 분말 및 유동성 농축물의 경우, 그의 적용 농도는 통상 0.1 내지 500ppm의 범위이다. 과립 및 분진의 경우에는, 어떠한 희석도 없이 그대로 적용한다. 본 발명에 의한 화합물이 전염병 방지용 살충제의 활성성분으로서 사용될 경우, 상기물은 유화성 농축물, 습윤성 분말 및 유동성 농축물과 같은 투여 형태로 조제하여, 0.1 내지 500ppm의 전형적인 농도로 물로 희석한 후 적용하거나; 오일 분무물, 에어로졸, 훈연제 및 독성 미끼와 같은 투여 형태로 조제하여, 어떠한 희석도 하지 않고 그대로 적용한다.When the compounds according to the invention are used as active ingredients of agricultural pesticides, their application is usually in the range of 0.1 to 100 g per 10 acres. In the case of emulsifiable concentrates, wettable powders and flowable concentrates which are used after dilution with water, their application concentration is usually in the range of 0.1 to 500 ppm. In the case of granules and dusts, they are applied without any dilution. When the compound according to the present invention is used as an active ingredient of an infectious insecticide, the water is prepared in dosage forms such as emulsifiable concentrates, wettable powders and flowable concentrates, and then diluted with water to a typical concentration of 0.1 to 500 ppm. do or; Formulated in dosage forms such as oil sprays, aerosols, smokers and toxic baits, they are applied without any dilution.

적용량과 적용 농도는 투여 형태의 종류, 적용 시간, 장소 및 방법, 해충의 종류, 손상 정도 등의 다양한 조건에 따라 다를 수 있으며, 상기 범위에 구애받지 않고 증가 또는 감소될 수 있다.The dosage and concentration may vary depending on various conditions such as the type of dosage form, time of application, location and method, type of pest, degree of damage, etc., and may be increased or decreased regardless of the above range.

본 발명은 또한 하기의 제조예, 제제예 및 시험예를 통해 자세히 기술될 것이다. 그러나 본 발명은 상기의 예에 한정되지는 않는다.The invention will also be described in detail through the following preparation examples, preparation examples and test examples. However, the present invention is not limited to the above examples.

하기는 다양한 제조 공정에 따른 본 발명에 의한 화합물의 제조예이다.The following are examples of the preparation of compounds according to the invention according to various preparation processes.

제조예 1Preparation Example 1

제조 공정 F에 의한 화합물 (2)의 제조Preparation of Compound (2) by Production Step F

디클로로메탄 5ml에 녹인 0.21g의 3,5-디클로로-4-(3-아미노프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠 및 0.07g의 트리에틸아민 용액에, 디클로로메탄 5ml에 녹인 0.11g의 4-클로로벤조일 클로라이드 용액을 빙냉 교반하에 적가한다. 실온에서 6시간 동안 교반한 후, 반응 혼합물을 물로 세척하고 농축하여 잔류물을 수득한다. 잔류물을 실리카 겔 크로마토그래피하여, 3,5-디클로로-4-(3-(4-클로로벤즈아미도)프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠 0.21g을 수득할 수 있다(수율 71%, m.p. 95.1℃).To 0.21 g of 3,5-dichloro-4- (3-aminopropyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene and 0.07 g of triethylamine solution dissolved in 5 ml of dichloromethane, 0.11 g of 4-chlorobenzoyl chloride solution dissolved in 5 ml of dichloromethane is added dropwise under ice-cooled stirring. After stirring for 6 hours at room temperature, the reaction mixture is washed with water and concentrated to give a residue. The residue was subjected to silica gel chromatography to give 0.21 g of 3,5-dichloro-4- (3- (4-chlorobenzamido) propyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene Can be obtained (yield 71%, mp 95.1 ° C.).

제조예 2Preparation Example 2

제조 공정 F에 의한 화합물 (7)의 제조Preparation of Compound (7) by Production Step F

디클로로메탄 5ml에 녹인 0.21g의 3,5-디클로로-4-(3-아미노프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠 및 0.07g의 트리에틸아민 용액에, 디클로로메탄 5ml에 녹인 0.11g의 4-트리플루오로메틸벤조일 클로라이드 용액을 빙냉 교반하에 적가한다. 실온에서 6시간 동안 교반한 후, 반응 혼합물을 물로 세척하고 농축하여 잔류물을 수득한다. 잔류물을 실리카 겔 크로마토그래피하여, 3,5-디클로로-4-(3-(4-트리플루오로메틸벤즈아미도)프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠 0.25g을 수득할 수 있다(수율 79%, m.p. 93.5℃).To 0.21 g of 3,5-dichloro-4- (3-aminopropyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene and 0.07 g of triethylamine solution dissolved in 5 ml of dichloromethane, 0.11 g of 4-trifluoromethylbenzoyl chloride solution dissolved in 5 ml of dichloromethane is added dropwise under ice-cooled stirring. After stirring for 6 hours at room temperature, the reaction mixture is washed with water and concentrated to give a residue. The residue was subjected to silica gel chromatography to give 3,5-dichloro-4- (3- (4-trifluoromethylbenzamido) propyloxy) -1- (3,3-dichloro-2-propenyloxy) 0.25 g of benzene can be obtained (yield 79%, mp 93.5 ° C).

제조예 3Preparation Example 3

제조 공정 F에 의한 화합물 (10)의 제조Preparation of Compound (10) by Production Step F

디클로로메탄 5ml에 녹인 0.15g의 4-트리플루오로메틸신남산 및 0.07g의 트리에틸아민 용액에, 0.14g의 1-에틸-3-(3-디메틸아미노프로필)카르보니이미드(WSC) 히드로클로라이드를 빙냉 교반하에 적가한다. 30분 동안 교반한 후, 디클로로메탄 5ml에 녹인 0.20g의 3,5-디클로로-4-(2-아미노에톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠을 적가한다. 실온에서 12시간 동안 교반한 후, 반응 혼합물을 농축하여 잔류물을 수득한다. 잔류물을 실리카 겔 크로마토그래피하여, 3,5-디클로로-4-(2-(4-트리플루오로메틸신남아미도)에톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠 0.20g을 수득할 수 있다(수율 63%, m.p. 109.4℃).0.14 g of 1-ethyl-3- (3-dimethylaminopropyl) carbonimide (WSC) hydrochloride was dissolved in 0.15 g of 4-trifluoromethylcinnamic acid and 0.07 g of triethylamine solution dissolved in 5 ml of dichloromethane. It is added dropwise under ice-cooled stirring. After stirring for 30 minutes, 0.20 g of 3,5-dichloro-4- (2-aminoethoxy) -1- (3,3-dichloro-2-propenyloxy) benzene dissolved in 5 ml of dichloromethane is added dropwise. . After stirring for 12 hours at room temperature, the reaction mixture is concentrated to give a residue. The residue was purified by silica gel chromatography to give 3,5-dichloro-4- (2- (4-trifluoromethylcinamido) ethoxy) -1- (3,3-dichloro-2-propenyloxy) 0.20 g of benzene can be obtained (yield 63%, mp 109.4 ° C.).

제조예 4Preparation Example 4

제조 공정 G에 의한 화합물 (24)의 제조Preparation of Compound (24) by Production Process G

디클로로메탄 5ml에 녹인 0.26g의 4-(2,6-디클로로-4-(3,3-디클로로-2-프로페닐옥시)페녹시)부티르산 및 0.07g의 트리에틸아민 용액에, 0.14g의 1-에틸-3-(3-디메틸아미노프로필)카르보디이미드(WSC) 히드로클로라이드를 빙냉 교반하에 적가한다. 30분 동안 교반한 후, 디클로로메탄 5ml에 녹인 0.12g의 4-트리플루오로메톡시아닐린을 적가한다. 실온에서 12시간 동안 교반한 후, 반응 혼합물을 농축하여 잔류물을 수득한다. 잔류물을 실리카 겔 크로마토그래피하여, 3,5-디클로로-4-(3-(N-(4-트리플루오로메톡시페닐)카르바모일)프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠 0.26g을 수득할 수 있다(수율 70%, m.p. 88.8℃).0.14 g of 1 in 0.26 g of 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyric acid and 0.07 g of triethylamine solution dissolved in 5 ml of dichloromethane Ethyl-3- (3-dimethylaminopropyl) carbodiimide (WSC) hydrochloride is added dropwise under ice-cooled stirring. After stirring for 30 minutes, 0.12 g of 4-trifluoromethoxyaniline dissolved in 5 ml of dichloromethane is added dropwise. After stirring for 12 hours at room temperature, the reaction mixture is concentrated to give a residue. The residue was subjected to silica gel chromatography to give 3,5-dichloro-4- (3- (N- (4-trifluoromethoxyphenyl) carbamoyl) propyloxy) -1- (3,3-dichloro-2 0.26 g of -propenyloxy) benzene can be obtained (yield 70%, mp 88.8 ° C.).

제조예 5Preparation Example 5

제조 공정 I에 의한 화합물 (25)의 제조Preparation of Compound (25) by Preparation Process I

디클로로메탄 5ml에 녹인 0.20g의 3,5-디클로로-4-(2-아미노에톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠 및 0.10g의 트리에틸아민 용액에, 디클로로메탄 5ml에 녹인 0.16g의 4-트리플루오로메톡시벤젠술포닐 클로라이드를 빙냉 교반하에 적가한다. 실온에서 6시간 동안 교반한 후, 반응 혼합물을 농축하여 잔류물을 수득한다. 잔류물을 실리카 겔 크로마토그래피하여, 3,5-디클로로-4-(2-(4-트리플루오로메톡시벤젠술폰아미도)에톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠 0.20g을 수득할 수 있다(수율 63%, nD 23.01.5470).To 0.20 g of 3,5-dichloro-4- (2-aminoethoxy) -1- (3,3-dichloro-2-propenyloxy) benzene and 0.10 g of triethylamine solution dissolved in 5 ml of dichloromethane, 0.16 g of 4-trifluoromethoxybenzenesulfonyl chloride dissolved in 5 ml of dichloromethane is added dropwise under ice-cooled stirring. After stirring for 6 hours at room temperature, the reaction mixture is concentrated to give a residue. The residue was subjected to silica gel chromatography to give 3,5-dichloro-4- (2- (4-trifluoromethoxybenzenesulfonamido) ethoxy) -1- (3,3-dichloro-2-propenyloxy 0.20 g of benzene can be obtained (yield 63%, n D 23.0 1.5470).

제조예 6Preparation Example 6

제조 공정 M에 의한 화합물 (26)의 제조Preparation of Compound (26) by Production Process M

톨루엔 10ml에 녹인 0.20g의 3,5-디클로로-4-(2-아미노에톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠 및 0.14g의 4-트리플루오로메톡시페닐 이소시아네이트 용액을 환류하에 가열하며 12시간 동안 교반한 다음 반응 혼합물을 농축하여 잔류물을 수득한다. 상기 잔류물을 실리카 켈 크로마토그래피하여 3,5-디클로로-4-(2-(N'-(4-트리플루오로메톡시페닐)우레이도)에톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠 0.15g을 수득할 수 있다(수율 46%, m.p. 125.4℃).0.20 g of 3,5-dichloro-4- (2-aminoethoxy) -1- (3,3-dichloro-2-propenyloxy) benzene and 0.14 g of 4-trifluoromethoxyphenyl dissolved in 10 ml of toluene The isocyanate solution is heated under reflux and stirred for 12 hours and then the reaction mixture is concentrated to give a residue. The residue was subjected to silica gel chromatography to give 3,5-dichloro-4- (2- (N '-(4-trifluoromethoxyphenyl) ureido) ethoxy) -1- (3,3-dichloro-2 0.15 g of propenyloxy) benzene can be obtained (yield 46%, mp 125.4 ° C.).

제조예 7Preparation Example 7

제조 공정 K에 의한 화합물 (28)의 제조Preparation of Compound (28) by Production Process K

톨루엔 10ml에 녹인 0.17g의 3,5-디클로로-4-(3-히드록시프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠, 0.09g의 4-클로로페닐 이소시아네이트 및 촉매량의 피리딘의 용액을 60℃ 내지 70℃로 가열하며 3시간 동안 교반한 다음 농축하여 잔류물을 수득한다. 상기 잔류물을 실리카 켈 크로마토그래피하여 3,5-디클로로-4-(3-(N-(4-클로로페닐)카르바모일옥시)프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠 0.19g을 수득할 수 있다(수율 77%, m.p. 54.3℃).0.17 g 3,5-dichloro-4- (3-hydroxypropyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene dissolved in 10 ml of toluene, 0.09 g of 4-chlorophenyl isocyanate, and The catalyst amount of pyridine solution is heated to 60 ° C. to 70 ° C., stirred for 3 hours and then concentrated to give a residue. The residue was subjected to silica gel chromatography to give 3,5-dichloro-4- (3- (N- (4-chlorophenyl) carbamoyloxy) propyloxy) -1- (3,3-dichloro-2-pro 0.19 g of phenyloxy) benzene can be obtained (yield 77%, mp 54.3 ° C.).

제조예 8Preparation Example 8

제조 공정 A에 의한 화합물 (7)의 제조Preparation of Compound (7) by Production Step A

2.0g의 3,5-디클로로-4-(3-(4-트리플루오로메틸벤즈아미도)프로필옥시)페놀, 0.68g의 탄산 칼륨 및 20ml의 N,N-디메틸포름아미드의 혼합물에, 0.71g의 1,1,3-트리클로로프로펜 및 5ml의 N,N-디메틸포름아미드의 혼합물을 실온에서 교반하면서 적가한다. 실온에서 6시간 동안 교반한 후, 반응 혼합물을 얼음물에 쏟아붓고 50ml의 디에틸 에테르로 2회 추출한다. 유기층을 취합하여 물로 세척하고 무수 황산 마그네슘으로 건조한 다음 농축하여, 조 결정을 수득한다. 상기 조 결정을 분쇄하고 n-헥산으로 세척하여, 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(4-트리플루오로메틸벤즈아미도)프로필옥시)벤젠 1.9g을 수득할 수 있다(수율 75%, m.p. 93.5℃).0.71 to a mixture of 2.0 g 3,5-dichloro-4- (3- (4-trifluoromethylbenzamido) propyloxy) phenol, 0.68 g potassium carbonate and 20 ml N, N-dimethylformamide A mixture of g 1,1,3-trichloropropene and 5 ml of N, N-dimethylformamide is added dropwise with stirring at room temperature. After stirring for 6 hours at room temperature, the reaction mixture is poured into iced water and extracted twice with 50 ml of diethyl ether. The organic layers are combined, washed with water, dried over anhydrous magnesium sulfate and concentrated to give crude crystals. The crude crystals were triturated and washed with n-hexane to give 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (4-trifluoromethylbenzamido 1.9 g)) propyloxy) benzene can be obtained (yield 75%, mp 93.5 ° C.).

제조예 9Preparation Example 9

제조 공정 F에 의한 화합물 (59)의 제조Preparation of Compound (59) by Production Process F

0.66g의 3-에틸-5-메틸-4-(3-(4-트리플루오로메틸벤즈아미도)프로필옥시)페놀, 0.29g의 탄산 칼륨 및 20ml의 N,N-디메틸포름아미드의 혼합물에, 0.28g의 1,1,3-트리클로로프로펜 및 5ml의 N,N-디메틸포름아미드의 혼합물을 실온에서 교반하면서 적가한다. 실온에서 6시간 동안 교반한 후, 반응 혼합물을 얼음물에 쏟아붓고 50ml의 디에틸 에테르로 2회 추출한다. 유기층을 취합하여 물로 세척하고 무수 황산 마그네슘으로 건조한 다음 농축하여, 조 결정을 수득한다. 상기 조 결정을 분쇄하고 n-헥산으로 세척하여, 3-에틸-5-메틸-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(4-트리플루오로메틸벤즈아미도)프로필옥시)벤젠 1.9g을 수득할 수 있다(수율 58%, m.p. 92.2℃).To a mixture of 0.66 g 3-ethyl-5-methyl-4- (3- (4-trifluoromethylbenzamido) propyloxy) phenol, 0.29 g potassium carbonate and 20 ml N, N-dimethylformamide , A mixture of 0.28 g of 1,1,3-trichloropropene and 5 ml of N, N-dimethylformamide was added dropwise while stirring at room temperature. After stirring for 6 hours at room temperature, the reaction mixture is poured into iced water and extracted twice with 50 ml of diethyl ether. The organic layers are combined, washed with water, dried over anhydrous magnesium sulfate and concentrated to give crude crystals. The crude crystals were triturated and washed with n-hexane to afford 3-ethyl-5-methyl-1- (3,3-dichloro-2-propenyloxy) -4- (3- (4-trifluoromethylbenz 1.9 g amido) propyloxy) benzene can be obtained (yield 58%, mp 92.2 ° C).

제조예 10Preparation Example 10

제조 공정 F에 의한 화합물 (67)의 제조Preparation of Compound (67) by Production Step F

0.96g의 4-(3-아미노프로필옥시)-3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)벤젠, 0.53g의 5-(트리플루오로메틸)2-피리딘카르복실산, 0.37g의 트리에틸아민 및 10ml의 클로로포름 혼합물에, 0.64g의 WSC 히드로클로라이드를 실온에서 교반하면서 첨가한다. 실온에서 6시간 동안 교반한 후, 반응 혼합물을 농축하여 잔류물을 수득한다. 이 잔류물을 겔 크로마토그래피하여, 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(5-(트리플루오로메틸)피콜린아미도)프로폭시)벤젠 0.15g을 수득할 수 있다(수율 10%, m.p. 55.1℃).0.96 g of 4- (3-aminopropyloxy) -3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) benzene, 0.53 g of 5- (trifluoromethyl) 2-pyridine To the carboxylic acid, 0.37 g triethylamine and 10 ml chloroform mixture, 0.64 g of WSC hydrochloride is added with stirring at room temperature. After stirring for 6 hours at room temperature, the reaction mixture is concentrated to give a residue. This residue was gel chromatographed to give 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (5- (trifluoromethyl) picolinamido) 0.15 g of propoxy) benzene can be obtained (yield 10%, mp 55.1 ° C.).

제조예 11Preparation Example 11

제조 공정 F에 의한 화합물 (34)의 제조Preparation of Compound (34) by Production Process F

0.35g의 4-(3-아미노프로필옥시)-3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)벤젠, 0.19g의 5-브로모-2-푸란카르복실산, 0.18ml의 트리에틸아민 및 10ml의 클로로포름 혼합물에, 0.23g의 WSC 히드로클로라이드를 실온에서 교반하면서 첨가한다. 실온에서 6시간 동안 교반한 후, 반응 혼합물을 농축하여 잔류물을 수득한다. 상기 잔류물을 50ml의 에틸 아세테이트에 녹이고, 에틸아세테이트층을 연속적으로 10% 염화 수소, 탄산 수소 나트륨 포화 수용액 및 포화 염수 용액으로 세척하고 무수 황산 마그네슘으로 건조시킨 다음 농축하여, 잔류물을 수득한다. 이 잔류물을 실리카 겔 크로마토그래피하여, 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(5-브로모-2-푸란카르복사미도)프로필옥시)벤젠 0.35g을 수득할 수 있다(수율 64%, nD 24.01.5918).0.35 g of 4- (3-aminopropyloxy) -3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) benzene, 0.19 g of 5-bromo-2-furancarboxylic acid To 0.18 ml of triethylamine and 10 ml of chloroform mixture, 0.23 g of WSC hydrochloride is added with stirring at room temperature. After stirring for 6 hours at room temperature, the reaction mixture is concentrated to give a residue. The residue is taken up in 50 ml of ethyl acetate and the ethyl acetate layer is washed successively with 10% hydrogen chloride, saturated aqueous sodium hydrogen carbonate solution and saturated brine solution, dried over anhydrous magnesium sulfate and concentrated to give a residue. This residue was subjected to silica gel chromatography to give 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (5-bromo-2-furancarboxamido) 0.35 g of propyloxy) benzene can be obtained (yield 64%, n D 24.0 1.5918).

제조예 12Preparation Example 12

제조 공정 F에 의한 화합물 (93)의 제조Preparation of Compound (93) by Production Process F

0.42g의 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(메틸아미노)프로필옥시)벤진, 0.18ml의 트리에틸아민 및 10ml의 클로로포름 혼합물에, 0.18ml의 4-(트리플루오로메틸)벤조일 클로라이드를 빙냉 교반하에 첨가한다. 실온에서 6시간 동안 교반한 후, 반응 혼합물을 농축하여 잔류물을 수득한다. 상기 잔류물을 50ml의 에틸 아세테이트에 녹이고, 에틸 아세테이트층을 연속적으로 10% 염화 수소, 탄산 수소 나트륨 포화 수용액 및 포화 염수 용액으로 세척하고 무수 황산 마그네슘으로 건조시킨 다음 농축하여, 잔류물을 수득한다. 이 잔류물을 실리카 겔 크로마토그래피하여, 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(N-메틸-4(트리플루오로메틸)벤즈아미도)프로필옥시)벤젠 0.35g을 수득할 수 있다(수율 55%, nD 24.51.5461).0.42 g of 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (methylamino) propyloxy) benzine, 0.18 ml of triethylamine and 10 ml of chloroform mixture To this, 0.18 ml of 4- (trifluoromethyl) benzoyl chloride are added under ice-cooled stirring. After stirring for 6 hours at room temperature, the reaction mixture is concentrated to give a residue. The residue is taken up in 50 ml of ethyl acetate and the ethyl acetate layer is washed successively with 10% hydrogen chloride, saturated aqueous sodium hydrogen carbonate solution and saturated brine solution, dried over anhydrous magnesium sulfate and concentrated to give a residue. This residue was purified by silica gel chromatography to give 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (N-methyl-4 (trifluoromethyl) benz 0.35 g of amido) propyloxy) benzene can be obtained (yield 55%, n D 24.5 1.5461).

제조예 13Preparation Example 13

제조 공정 F에 의한 화합물 (100)의 제조Preparation of Compound (100) by Production Process F

0.35g의 4-(3-아미노프로필옥시)-3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)벤젠, 0.17g의 4-클로로페닐아세트산, 0.18ml의 트리에틸아민 및 10ml의 디클로로메탄 혼합물에, 0.23g의 WSC 히드로클로라이드를 실온에서 교반하면서 첨가한다. 실온에서 6시간 동안 교반한 후, 반응 혼합물을 농축하여 잔류물을 수득한다. 상기 잔류물을 50ml의 에틸 아세테이트에 녹이고, 에틸 아세테이트층을 연속적으로 10% 염화 수소, 탄산 수소 나트륨 포화 수용액 및 포화 염수 용액으로 세척하고 무수 황산 마그네슘으로 건조시킨 다음 농축하여, 잔류물을 수득한다. 이 잔류물을 실리카 겔 크로마토그래피하여, 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(4-클로로페닐아세트아미도)프로필옥시)벤젠 0.35g을 수득할 수 있다(수율 70%, m.p. 108.4).0.35 g 4- (3-aminopropyloxy) -3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) benzene, 0.17 g 4-chlorophenylacetic acid, 0.18 ml triethyl To the amine and 10 ml dichloromethane mixture, 0.23 g of WSC hydrochloride is added with stirring at room temperature. After stirring for 6 hours at room temperature, the reaction mixture is concentrated to give a residue. The residue is taken up in 50 ml of ethyl acetate and the ethyl acetate layer is washed successively with 10% hydrogen chloride, saturated aqueous sodium hydrogen carbonate solution and saturated brine solution, dried over anhydrous magnesium sulfate and concentrated to give a residue. This residue was subjected to silica gel chromatography to give 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (4-chlorophenylacetamido) propyloxy) benzene 0.35 g can be obtained (yield 70%, mp 108.4).

제조예 14Preparation Example 14

제조 공정 F에 의한 화합물 (127)의 제조Preparation of Compound (127) by Preparation Process F

10ml의 클로로포름에 녹인 0.20g의 5-(2,6-디클로로-4-(3,3-디클로로-2-프로페닐옥시)페녹시)발레르산 및 0.05g의 디프로파길아민의 용액에, 0.11g의 WSC 히드로클로라이드를 실온에서 교반하면서 첨가한다. 실온에서 24시간 동안 교반한 후, 반응 혼합물을 농축하여 잔류물을 수득한다. 이 잔류물을 실리카 겔 크로마토그래피하여, 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(N,N-디프로파길카르바모일)부틸옥시)벤젠 0.21g을 수득할 수 있다(수율 92%, nD 25.01.5481).0.11 g of a solution of 0.20 g of 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) valeric acid and 0.05 g of dipropargylamine dissolved in 10 ml of chloroform g of WSC hydrochloride is added with stirring at room temperature. After stirring for 24 hours at room temperature, the reaction mixture is concentrated to give a residue. This residue was subjected to silica gel chromatography to give 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (N, N-dipropargylcarbamoyl) butyl 0.21 g of oxy) benzene can be obtained (yield 92%, n D 25.0 1.5481).

제조예 15Preparation Example 15

제조 공정 L에 의한 화합물 (129)의 제조Preparation of Compound (129) by Preparation Process L

0.33g의 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(아미노프로필옥시)벤젠 및 10ml의 피리딘의 혼합물을 0℃로 냉각시키고, 0.10g의 메틸클로로포르메이트를 교반하에 천천히 적가한다. 반응 혼합물을 0℃에서 1시간 동안 교반한 후, 온도를 서서히 실온으로 상승시키고, 반응 혼합물을 실온에서 6시간 동안 더 교반한다. 반응 혼합물을 10%의 염화 수소에 쏟아붓고, 혼합물을 50ml의 에틸 아세테이트로 2회에 걸쳐 추출한다. 에틸 아세테이트층을 취합하여 물로 세척하고 무수 황산 마그네슘으로 건조시킨 다음 농축하여, 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-메톡시카르보닐아미노)프로필옥시) 벤젠 0.30g을 수득할 수 있다(수율 74%, nD 25.51.5421).A mixture of 0.33 g of 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (aminopropyloxy) benzene and 10 ml of pyridine is cooled to 0 ° C. and 0.10 g of methylchloroformate is slowly added dropwise under stirring The reaction mixture is stirred at 0 ° C. for 1 hour, then the temperature is slowly raised to room temperature and the reaction mixture is further stirred at room temperature for 6 hours. Pour into% hydrogen chloride and extract the mixture twice with 50 ml of ethyl acetate The ethyl acetate layers were combined, washed with water, dried over anhydrous magnesium sulfate and concentrated to give 3,5-dichloro-1- ( 0.30 g of 3,3-dichloro-2-propenyloxy) -4- (3-methoxycarbonylamino) propyloxy) benzene can be obtained (yield 74%, n D 25.5 1.5421).

하기는 본 발명에 의한 화합물의 특정예를, 그의 화합물 번호 및 물리적 성질(측정될 경우)과 함께 기술하고 있다.The following describes specific examples of compounds according to the invention, together with their compound numbers and physical properties (when measured).

(1) 3,5-디클로로-4-(3-벤즈아미도프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠nD 23.01.5860(1) 3,5-dichloro-4- (3-benzamidopropyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene n D 23.0 1.5860

(2) 3,5-디클로로-4-(3-(4-클로로벤즈아미도)프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 95.1℃(2) 3,5-dichloro-4- (3- (4-chlorobenzamido) propyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 95.1 ℃

(3) 3,5-디클로로-4-(2-(4-트리플루오로메톡시벤즈아미도)에톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 81.0℃(3) 3,5-dichloro-4- (2- (4-trifluoromethoxybenzamido) ethoxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 81.0 ℃

(4) 3,5-디클로로-4-(3-(4-트리플루오로메톡시벤즈아미도)프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 93.8℃(4) 3,5-dichloro-4- (3- (4-trifluoromethoxybenzamido) propyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 93.8 ℃

(5) 3,5-디클로로-4-(3-(4-플루오로벤즈아미도)프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠nD 24.51.5800(5) 3,5-dichloro-4- (3- (4-fluorobenzamido) propyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene n D 24.5 1.5800

(6) 3,5-디클로로-4-(3-(4-브로모벤즈아미도)프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 102.7℃(6) 3,5-dichloro-4- (3- (4-bromobenzamido) propyloxy) -1- (3,3-dichloro-2-propenyloxy) benzenem.p. 102.7 ℃

(7) 3,5-디클로로-4-(3-(4-트리플루오로메틸벤즈아미도)프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 93.5℃(7) 3,5-dichloro-4- (3- (4-trifluoromethylbenzamido) propyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 93.5 ℃

(8) 3,5-디클로로-4-(3-(4-에톡시벤즈아미도)프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 120.6℃(8) 3,5-dichloro-4- (3- (4-ethoxybenzamido) propyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 120.6 ℃

(9) 3,5-디클로로-4-(3-(4-이소프로폭시벤즈아미도)프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 91.8℃(9) 3,5-dichloro-4- (3- (4-isopropoxybenzamido) propyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 91.8 ℃

(10) 3,5-디클로로-4-(2-(4-트리플루오로메틸신남아미도)에톡시-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 109.4℃(10) 3,5-dichloro-4- (2- (4-trifluoromethylcinamido) ethoxy-1- (3,3-dichloro-2-propenyloxy) benzene m.p. 109.4 ° C

(11) 3,5-디클로로-4-(3-(4-트리플루오로메틸신남아미도)프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 116.6℃(11) 3,5-dichloro-4- (3- (4-trifluoromethylcinamido) propyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 116.6 ℃

(12) 3,5-디클로로-4-(3-(2-클로로벤즈아미도)프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 70.3℃(12) 3,5-dichloro-4- (3- (2-chlorobenzamido) propyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 70.3 ℃

(13) 3,5-디클로로-4-(3-(3-클로로벤즈아미도)프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 70.3℃(13) 3,5-dichloro-4- (3- (3-chlorobenzamido) propyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 70.3 ℃

(14) 3,5-디클로로-4-(3-(2,4-디클로로벤즈아미도)프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 118.5℃(14) 3,5-dichloro-4- (3- (2,4-dichlorobenzamido) propyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 118.5 ℃

(15) 3,5-디클로로-4-(3-(2,6-디클로로벤즈아미도)프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 124.6℃(15) 3,5-dichloro-4- (3- (2,6-dichlorobenzamido) propyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 124.6 ℃

(16) 3,5-디클로로-4-(3-(2,4,6-트리클로로벤즈아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 126.1℃(16) 3,5-dichloro-4- (3- (2,4,6-trichlorobenzamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 126.1 ℃

(17) 3,5-디클로로-4-(3-(2-트리플루오로메틸벤즈아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 98.9℃(17) 3,5-dichloro-4- (3- (2-trifluoromethylbenzamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 98.9 ℃

(18) 3,5-디클로로-4-(3-(3-트리플루오로메틸벤즈아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 73.5℃(18) 3,5-dichloro-4- (3- (3-trifluoromethylbenzamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 73.5 ℃

(19) 3,5-디클로로-4-(3-(3,5-트리플루오로메틸벤즈아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 110.4℃(19) 3,5-dichloro-4- (3- (3,5-trifluoromethylbenzamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 110.4 ℃

(20) 3,5-디클로로-4-(3-(4-tert-부틸벤즈아미도)프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 109.5℃(20) 3,5-dichloro-4- (3- (4-tert-butylbenzamido) propyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 109.5 ℃

(21) 3,5-디클로로-4-(3-(3,4-디클로로벤즈아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 85.9℃(21) 3,5-dichloro-4- (3- (3,4-dichlorobenzamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 85.9 ℃

(22) 3,5-디클로로-4-(3-(4-니트로벤즈아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 136.0℃(22) 3,5-dichloro-4- (3- (4-nitrobenzamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 136.0 ℃

(23) 3,5-디클로로-4-(3-(4-시아노벤즈아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 111.7℃(23) 3,5-dichloro-4- (3- (4-cyanobenzamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 111.7 ℃

(24) 3,5-디클로로-4-(3-(N-(4-트리플루오로메톡시페닐)카르바모일)프로폭시-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 88.8℃(24) 3,5-dichloro-4- (3- (N- (4-trifluoromethoxyphenyl) carbamoyl) propoxy-1- (3,3-dichloro-2-propenyloxy) benzene mp 88.8 ℃

(25) 3,5-디클로로-4-(2-(4-트리플루오로메톡시벤젠술폭아미도)에톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠nD 23.01.5470(25) 3,5-dichloro-4- (2- (4-trifluoromethoxybenzenesulphamido) ethoxy) -1- (3,3-dichloro-2-propenyloxy) benzene n D 23.0 1.5470

(26) 3,5-디클로로-4-(2-(N'-(4-트리플루오로메톡시페닐)우레이도)에톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 125.4℃(26) 3,5-dichloro-4- (2- (N '-(4-trifluoromethoxyphenyl) ureido) ethoxy) -1- (3,3-dichloro-2-propenyloxy) benzene mp 125.4 ℃

(27) 3,5-디클로로-4-(3-(N-(4-페닐카르바모일옥시)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠nD 24.51.5777(27) 3,5-dichloro-4- (3- (N- (4-phenylcarbamoyloxy) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene n D 24.5 1.5777

(28) 3,5-디클로로-4-(3-(N-(4-클로로페닐)카르바모일옥시)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 54.3℃(28) 3,5-dichloro-4- (3- (N- (4-chlorophenyl) carbamoyloxy) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 54.3 ℃

(29) 3,5-디클로로-4-(2-(N-(4-클로로페닐)카르바모일옥시)에톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 105.5℃(29) 3,5-dichloro-4- (2- (N- (4-chlorophenyl) carbamoyloxy) ethoxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 105.5 ℃

(30) 3,5-디클로로-4-(2-(N-(4-트리플루오로메톡시페닐)카르바모일옥시)에톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠nD 24.51.5446(30) 3,5-dichloro-4- (2- (N- (4-trifluoromethoxyphenyl) carbamoyloxy) ethoxy) -1- (3,3-dichloro-2-propenyloxy) Benzene n D 24.5 1.5446

(31) 3,5-디클로로-4-(3-(6-클로로니코틴아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 85.6℃(31) 3,5-dichloro-4- (3- (6-chloronicotinamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 85.6 ℃

(32) 3,5-디클로로-4-(4-(4-트리플루오로메틸벤즈아미도)부톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 90.5℃(32) 3,5-dichloro-4- (4- (4-trifluoromethylbenzamido) butoxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 90.5 ℃

(33) 3,5-디클로로-4-(3-티오펜-2-카르복사미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠nD 24.01.6026(33) 3,5-dichloro-4- (3-thiophene-2-carboxamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene n D 24.0 1.6026

(34) 3,5-디클로로-4-(3-(5-브로모푸란-2-카르복사미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠nD 24.01.5918(34) 3,5-dichloro-4- (3- (5-bromofuran-2-carboxamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene n D 24.0 1.5918

(35) 3,5-디클로로-4-(3-(5-클로로인돌-2-카르복사미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 153.9℃(35) 3,5-dichloro-4- (3- (5-chloroindole-2-carboxamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 153.9 ℃

(36) 3,5-디클로로-4-(3-(4-클로로벤즈아미도)프로폭시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠(36) 3,5-dichloro-4- (3- (4-chlorobenzamido) propoxy) -1- (3,3-dibromo-2-propenyloxy) benzene

(37) 3,5-디브로모-4-(3-(4-클로로벤즈아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(37) 3,5-dibromo-4- (3- (4-chlorobenzamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(38) 3,5-디메틸-4-(3-(4-클로로벤즈아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(38) 3,5-dimethyl-4- (3- (4-chlorobenzamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(39) 3,5-디클로로-4-(3-(4-클로로벤즈아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(39) 3,5-dichloro-4- (3- (4-chlorobenzamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(40) 3-클로로-5-플루오로-4-(3-(4-클로로벤즈아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(40) 3-chloro-5-fluoro-4- (3- (4-chlorobenzamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(41) 3-클로로-5-메틸-4-(3-(4-클로로벤즈아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(41) 3-chloro-5-methyl-4- (3- (4-chlorobenzamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(42) 3-클로로-5-에틸-4-(3-(4-클로로벤즈아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(42) 3-chloro-5-ethyl-4- (3- (4-chlorobenzamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(43) 3-에틸-5-메틸-4-(3-(4-클로로벤즈아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(43) 3-ethyl-5-methyl-4- (3- (4-chlorobenzamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(44) 3,5-디클로로-4-(4-(4-클로로벤즈아미도)부톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 96.5℃(44) 3,5-dichloro-4- (4- (4-chlorobenzamido) butoxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 96.5 ℃

(45) 3,5-디클로로-4-(4-(4-클로로벤즈아미도)부톡시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠(45) 3,5-dichloro-4- (4- (4-chlorobenzamido) butoxy) -1- (3,3-dibromo-2-propenyloxy) benzene

(46) 3,5-디브로모-4-(4-(4-클로로벤즈아미도)부톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(46) 3,5-dibromo-4- (4- (4-chlorobenzamido) butoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(47) 3,5-디메틸-4-(4-(4-클로로벤즈아미도)부톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(47) 3,5-dimethyl-4- (4- (4-chlorobenzamido) butoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(48) 3,5-디에틸-4-(4-(4-클로로벤즈아미도)부톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(48) 3,5-diethyl-4- (4- (4-chlorobenzamido) butoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(49) 3-클로로-5-플루오로-4-(4-(4-클로로벤즈아미도)부톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(49) 3-chloro-5-fluoro-4- (4- (4-chlorobenzamido) butoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(50) 3-클로로-5-메틸-4-(4-(4-클로로벤즈아미도)부톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(50) 3-chloro-5-methyl-4- (4- (4-chlorobenzamido) butoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(51) 3-클로로-5-에틸-4-(4-(4-클로로벤즈아미도)부톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(51) 3-chloro-5-ethyl-4- (4- (4-chlorobenzamido) butoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(52) 3-에틸-5-메틸-4-(4-(4-클로로벤즈아미도)부톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(52) 3-ethyl-5-methyl-4- (4- (4-chlorobenzamido) butoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(53) 3,5-디클로로-4-(3-(4-트리플루오로메틸벤즈아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(53) 3,5-dichloro-4- (3- (4-trifluoromethylbenzamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(54) 3,5-디브로모-4-(3-(4-트리플루오로메틸벤즈아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(54) 3,5-dibromo-4- (3- (4-trifluoromethylbenzamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(55) 3,5-디메틸-4-(3-(4-트리플루오로메틸벤즈아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(55) 3,5-dimethyl-4- (3- (4-trifluoromethylbenzamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(56) 3,5-디에틸-4-(3-(4-트리플루오로메틸벤즈아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 99.5℃(56) 3,5-diethyl-4- (3- (4-trifluoromethylbenzamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 99.5 ℃

(57) 3-클로로-5-플루오로-4-(3-(4-트리플루오로메틸벤즈아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(57) 3-chloro-5-fluoro-4- (3- (4-trifluoromethylbenzamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(58) 3-클로로-5-메틸-4-(3-(4-트리플루오로메틸벤즈아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 91.0℃(58) 3-chloro-5-methyl-4- (3- (4-trifluoromethylbenzamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 91.0 ℃

(59) 3-에틸-5-메틸-4-(3-(4-트리플루오로메틸벤즈아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 92.2℃(59) 3-ethyl-5-methyl-4- (3- (4-trifluoromethylbenzamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 92.2 ℃

(60) 3,5-디클로로-4-(4-(4-트리플루오로메틸벤즈아미도)부톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(60) 3,5-dichloro-4- (4- (4-trifluoromethylbenzamido) butoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(61) 3,5-디브로모-4-(4-(4-트리플루오로메틸벤즈아미도)부톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(61) 3,5-dibromo-4- (4- (4-trifluoromethylbenzamido) butoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(62) 3,5-디메틸-4-(4-(4-트리플루오로메틸벤즈아미도)부톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(62) 3,5-dimethyl-4- (4- (4-trifluoromethylbenzamido) butoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(63) 3,5-디에틸-4-(4-(4-트리플루오로메틸벤즈아미도)부톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(63) 3,5-diethyl-4- (4- (4-trifluoromethylbenzamido) butoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(64) 3-클로로-5-플루오로-4-(4-(4-트리플루오로메틸벤즈아미도)부톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(64) 3-chloro-5-fluoro-4- (4- (4-trifluoromethylbenzamido) butoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(65) 3-클로로-5-메틸-4-(4-(4-트리플루오로메틸벤즈아미도)부톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(65) 3-chloro-5-methyl-4- (4- (4-trifluoromethylbenzamido) butoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(66) 3-에틸-5-메틸-4-(4-(4-트리플루오로메틸벤즈아미도)부톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(66) 3-ethyl-5-methyl-4- (4- (4-trifluoromethylbenzamido) butoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(67) 3,5-디클로로-4-(3-(5-트리플루오로메틸피콜린아미도)프로폭시시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠m.p. 55.1℃(67) 3,5-dichloro-4- (3- (5-trifluoromethylpicolinamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene m.p. 55.1 ℃

(68) 3,5-디클로로-4-(3-(5-트리플루오로메틸피콜린아미도)프로폭시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠(68) 3,5-dichloro-4- (3- (5-trifluoromethylpicolinamido) propoxy) -1- (3,3-dibromo-2-propenyloxy) benzene

(69) 3,5-디브로모-4-(3-(5-트리플루오로메틸피콜린아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(69) 3,5-dibromo-4- (3- (5-trifluoromethylpicolinamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(70) 3,5-디메틸-4-(3-(5-트리플루오로메틸피콜린아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(70) 3,5-dimethyl-4- (3- (5-trifluoromethylpicolinamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(71) 3,5-디에틸-4-(3-(5-트리플루오로메틸피콜린아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(71) 3,5-diethyl-4- (3- (5-trifluoromethylpicolinamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(72) 3-클로로-5-플루오로-4-(3-(5-트리플루오로메틸피콜린아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(72) 3-chloro-5-fluoro-4- (3- (5-trifluoromethylpicolinamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(73) 3-클로로-5-메틸-4-(3-(5-트리플루오로메틸피콜린아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(73) 3-chloro-5-methyl-4- (3- (5-trifluoromethylpicolinamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(74) 3-에틸-5-메틸-4-(3-(5-트리플루오로메틸피콜린아미도)프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(74) 3-ethyl-5-methyl-4- (3- (5-trifluoromethylpicolinamido) propoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(75) 3,5-디클로로-4-(4-(5-트리플루오로메틸피콜린아미도)부틸옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(75) 3,5-dichloro-4- (4- (5-trifluoromethylpicolinamido) butyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(76) 3,5-디클로로-4-(4-(5-트리플루오로메틸피콜린아미도)부틸옥시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠(76) 3,5-dichloro-4- (4- (5-trifluoromethylpicolinamido) butyloxy) -1- (3,3-dibromo-2-propenyloxy) benzene

(77) 3,5-디브로모-4-(4-(5-트리플루오로메틸피콜린아미도)부틸옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(77) 3,5-dibromo-4- (4- (5-trifluoromethylpicolinamido) butyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(78) 3,5-디메틸-4-(4-(5-트리플루오로메틸피콜린아미도)부틸옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(78) 3,5-dimethyl-4- (4- (5-trifluoromethylpicolinamido) butyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(79) 3,5-디에틸-4-(4-(5-트리플루오로메틸피콜린아미도)부틸옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(79) 3,5-diethyl-4- (4- (5-trifluoromethylpicolinamido) butyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(80) 3-클로로-5-플루오로-4-(4-(5-트리플루오로메틸피콜린아미도)부틸옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(80) 3-chloro-5-fluoro-4- (4- (5-trifluoromethylpicolinamido) butyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(81) 3-클로로-5-메틸-4-(4-(5-트리플루오로메틸피콜린아미도)부틸옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(81) 3-chloro-5-methyl-4- (4- (5-trifluoromethylpicolinamido) butyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(82) 3-에틸-5-메틸-4-(4-(5-트리플루오로메틸피콜린아미도)부틸옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠(82) 3-ethyl-5-methyl-4- (4- (5-trifluoromethylpicolinamido) butyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene

(83) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(5-메틸-1,4-벤조디옥산-6-카르복사미도)프로폭시)벤젠m.p. 120.8℃(83) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (5-methyl-1,4-benzodioxane-6-carboxamido) pro Foxy) benzene mp 120.8 ℃

(84) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(2-피라진카르복사미도)프로폭시)벤젠nD 28.01.5825(84) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (2-pyrazinecarboxamido) propoxy) benzene n D 28.0 1.5825

(85) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(4-피리다진카르복사미도)프로폭시)벤젠유리질(85) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (4-pyridazinecarboxamido) propoxy) benzeneglass

(86) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(1-메틸-2-인돌카르복사미도)프로폭시)벤젠m.p. 123.3℃(86) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (1-methyl-2-indolecarboxamido) propoxy) benzene m.p. 123.3 ℃

(87) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(6,6-디메틸-5,6-디히드로-4H-피란-4-온-2-카르복사미도)프로폭시)벤젠nD 28.01.5612(87) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (6,6-dimethyl-5,6-dihydro-4H-pyran-4- On-2-carboxamido) propoxy) benzene n D 28.0 1.5612

(88) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(4-옥소-4H-1-벤조피란-2-카르복사미도)프로폭시)벤젠m.p. 165.7℃(88) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (4-oxo-4H-1-benzopyran-2-carboxamido) propoxy Benzene mp 165.7 ℃

(89) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(1-메틸-2-피롤카르복사미도)프로폭시)벤젠nD 28.01.5772(89) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (1-methyl-2-pyrrolecarboxamido) propoxy) benzene n D 28.0 1.5772

(90) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(2-퀴놀린카르복시아미도)프로폭시)벤젠m.p. 145.8℃(90) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (2-quinolinecarboxamido) propoxy) benzene m.p. 145.8 ℃

(91) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(5-메틸-2-피라진카르복사미도)프로폭시)벤젠m.p. 109.0℃(91) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (5-methyl-2-pyrazinecarboxamido) propoxy) benzene m.p. 109.0 ℃

(92) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(N-메틸-4-(트리플루오로메틸)벤즈아미도)프로폭시)벤젠nD 26.01.5417(92) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (N-methyl-4- (trifluoromethyl) benzamido) propoxy) Benzene n D 26.0 1.5417

(93) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(N-메틸-4-(트리플루오로메틸)벤즈아미도)프로폭시)벤젠nD 24.51.5461(93) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (N-methyl-4- (trifluoromethyl) benzamido) propoxy) Benzene n D 24.5 1.5461

(94) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(2-푸란카르복사미도)프로폭시)벤젠nD 24.51.5682(94) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (2-furancarboxamido) propoxy) benzene n D 24.5 1.5682

(95) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(3-푸란카르복사미드)프로폭시)벤젠nD 24.51.5695(95) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (3-furancarboxamide) propoxy) benzene n D 24.5 1.5695

(96) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(3-티오펜카르복사미도)프로폭시)벤젠nD 24.51.5824(96) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (3-thiophenecarboxamido) propoxy) benzene n D 24.5 1.5824

(97) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(5-메틸-티오펜카르복사미도)프로폭시)벤젠m.p. 85.4℃(97) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (5-methyl-thiophenecarboxamido) propoxy) benzene m.p. 85.4 ℃

(98) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(4-프로필벤즈아미도)프로폭시)벤젠m.p. 92.9℃(98) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (4-propylbenzamido) propoxy) benzene m.p. 92.9 ℃

(99) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(6-메틸-3-피리딘카르복사미도)프로폭시)벤젠m.p. 94.8℃(99) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (6-methyl-3-pyridinecarboxamido) propoxy) benzene m.p. 94.8 ℃

(100) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(4-클로로페닐아세아미도)프로폭시)벤젠m.p. 108.40℃(100) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (4-chlorophenylaceamido) propoxy) benzene m.p. 108.40 ℃

(101) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(3-(트리플루오로메틸)페닐아세트아미도)프로폭시)벤젠m.p. 88.7℃(101) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (3- (trifluoromethyl) phenylacetamido) propoxy) benzene m.p. 88.7 ℃

(102) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(N-이소프로필-4-(트리플루오로메틸)벤즈아미도)부톡시)벤젠nD 24.51.5394(102) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (N-isopropyl-4- (trifluoromethyl) benzamido) butoxy Benzene n D 24.5 1.5394

(103) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(N-(4-트리플루오로메틸)페닐)카르바모일)프로폭시)벤젠m.p. 112.8℃(103) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (N- (4-trifluoromethyl) phenyl) carbamoyl) propoxy) Benzene mp 112.8 ℃

(104) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(N-(4-트리플루오로메틸)페닐)카르바모일)부톡시)벤젠m.p. 111.5℃(104) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (N- (4-trifluoromethyl) phenyl) carbamoyl) butoxy) Benzene mp 111.5 ℃

(105) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(1-메틸-5-니트로-4-피라졸레카르복사미도)프로폭시)벤젠m.p. 122.2℃(105) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (1-methyl-5-nitro-4-pyrazolecarboxamido) propoxy) Benzene mp 122.2 ℃

(106) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(3-퀴놀린카르복사미도)프로폭시)벤젠m.p. 115.9℃(106) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (3-quinolinecarboxamido) propoxy) benzene m.p. 115.9 ℃

(107) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(5-니트로-2-푸란카르복사미도)프로폭시)벤젠nD 21.01.5850(107) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (5-nitro-2-furancarboxamido) propoxy) benzene n D 21.0 1.5850

(108) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(5-(트리플루오로메틸)-2-피리딘카르복사미도)프로폭시)벤젠m.p. 66.8℃(108) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (5- (trifluoromethyl) -2-pyridinecarboxamido) propoxy) Benzene mp 66.8 ℃

(109) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(N-(5-브로모-2-티아졸)카르바모일)프로폭시)벤젠m.p. 164.0℃(109) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (N- (5-bromo-2-thiazole) carbamoyl) propoxy Benzene mp 164.0 ℃

(110) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(4-클로로벤젠술폰아미도)부톡시)벤젠nD 21.51.5745(110) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (4-chlorobenzenesulfonamido) butoxy) benzenen D 21.5 1.5745

(111) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(5-브로모-2-푸란카르복사미도)부톡시)벤젠nD 21.51.5801(111) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (5-bromo-2-furancarboxamido) butoxy) benzenen D 21.5 1.5801

(112) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(5-메틸-2-티오펜카르복사미도)부톡시)벤젠m.p. 105.2℃(112) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (5-methyl-2-thiophenecarboxamido) butoxy) benzenem.p. 105.2 ℃

(113) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(3-퀴놀린카르복사미도)부톡시)벤젠m.p. 115.9℃(113) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (3-quinolinecarboxamido) butoxy) benzenem.p. 115.9 ℃

(114) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(디프로필카르바모일)부톡시)벤젠nD 26.51.5291(114) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (dipropylcarbamoyl) butoxy) benzenen D 26.5 1.5291

(115) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(5-(디프로필카르바모일)펜톡시)벤젠nD 24.01.5271(115) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (5- (dipropylcarbamoyl) pentoxy) benzenen D 24.0 1.5271

(116) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(디에틸카르바모일)부톡시)벤젠nD 25.01.5386(116) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (diethylcarbamoyl) butoxy) benzenen D 25.0 1.5386

(117) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-트리플루오로아세트아미도)프로폭시)벤젠m.p. 68.1℃(117) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3-trifluoroacetamido) propoxy) benzene m.p. 68.1 ℃

(118) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-트리플루오로메탄술포닐)프로폭시)벤젠m.p. 47.2℃(118) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3-trifluoromethanesulfonyl) propoxy) benzene m.p. 47.2 ℃

(119) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-아세트아미도프로폭시)벤젠m.p. 77.8℃(119) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3-acetamidopropoxy) benzene m.p. 77.8 ℃

(120) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(1-피페리딜카르보닐)부톡시)벤젠nD 24.51.5423(120) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (1-piperidylcarbonyl) butoxy) benzenen D 24.5 1.5423

(121) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(1-피롤리디닐카르보닐)부톡시)벤젠nD 24.51.5537(121) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (1-pyrrolidinylcarbonyl) butoxy) benzene n D 24.5 1.5537

(122) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(2-(1-피페리딜카르보닐)에톡시)벤젠nD 27.01.5517(122) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (2- (1-piperidylcarbonyl) ethoxy) benzene n D 27.0 1.5517

(123) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(1-피페리딜카르보닐)프로폭시)벤젠nD 25.01.5510(123) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (1-piperidylcarbonyl) propoxy) benzene n D 25.0 1.5510

(124) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(N,N-디알킬카르바모일)부톡시)벤젠nD 26.51.5432(124) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (N, N-dialkylcarbamoyl) butoxy) benzenen D 26.5 1.5432

(125) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(5-(1-피페리딜카르보닐)펜톡시)벤젠nD 24.01.5395(125) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (5- (1-piperidylcarbonyl) pentoxy) benzene n D 24.0 1.5395

(126) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(5-(N,N-디알킬카르바모일)펜톡시)벤젠nD 24.01.5396(126) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (5- (N, N-dialkylcarbamoyl) pentoxy) benzenen D 24.0 1.5396

(127) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(N,N-디프로파길카르바모일)부톡시)벤젠nD 25.01.5481(127) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (N, N-dipropargylcarbamoyl) butoxy) benzenen D 25.0 1.5481

(128) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(4-모르폴리닐카르보닐)부톡시)벤젠nD 25.51.5450(128) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (4-morpholinylcarbonyl) butoxy) benzenen D 25.5 1.5450

(129) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(메톡시카르보닐아미노)프로폭시)벤젠nD 25.51.5421(129) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (methoxycarbonylamino) propoxy) benzene n D 25.5 1.5421

(130) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(메톡시카르보닐)부톡시)벤젠nD 24.51.5440(130) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (methoxycarbonyl) butoxy) benzenen D 24.5 1.5440

(131) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(에톡시카르보닐)부톡시)벤젠nD 24.51.5375(131) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (ethoxycarbonyl) butoxy) benzenen D 24.5 1.5375

(132) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(프로필옥시카르보닐아미노)부톡시)벤젠nD 24.51.5339(132) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (propyloxycarbonylamino) butoxy) benzenen D 24.5 1.5339

(133) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(피발라미도)프로톡시)벤젠nD 23.01.5407(133) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (pivalamido) propoxy) benzenen D 23.0 1.5407

(134) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(2,4-비스(트리플루오로메틸)벤즈아미도)프로폭시)벤젠(134) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (2,4-bis (trifluoromethyl) benzamido) propoxy) benzene

(135) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(2,4-비스(트리플루오로메틸)벤즈아미도)부티록시)벤젠(135) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (2,4-bis (trifluoromethyl) benzamido) butyoxy) benzene

(136) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(2-플루오로-4-(트리플루오로메틸)벤즈아미도)프로폭시)벤젠(136) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (2-fluoro-4- (trifluoromethyl) benzamido) propoxy )benzene

(137) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(2-플루오로-4-(트리플루오로메틸)벤즈아미도)부티록시)벤젠(137) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (2-fluoro-4- (trifluoromethyl) benzamido) butyoxy )benzene

(138) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(2-니트로-4-(트리플루오로메틸)벤즈아미도)프로폭시)벤젠(138) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (2-nitro-4- (trifluoromethyl) benzamido) propoxy) benzene

(139) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(2-니트로-4-(트리플루오로메틸)벤즈아미도)부티록시)벤젠(139) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (2-nitro-4- (trifluoromethyl) benzamido) butyoxy) benzene

(140) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(4-클로로-2-플루오로벤즈아미도)프로폭시)벤젠(140) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (4-chloro-2-fluorobenzamido) propoxy) benzene

(141) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(4-클로로로-2-(플루오로벤즈아미도)부티록시)벤젠(141) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (4-chloro-2- (fluorobenzamido) butyoxy) benzene

(142) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(2-클로로-5-(트리플루오로메틸)벤즈아미도)프로폭시)벤젠(142) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (2-chloro-5- (trifluoromethyl) benzamido) propoxy) benzene

(143) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(2-클로로-5-(트리플루오로메틸)벤즈아미도)부티록시)벤젠(143) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (2-chloro-5- (trifluoromethyl) benzamido) butyoxy) benzene

(144) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(2,5-디클로로벤즈아미도)프로폭시)벤젠(144) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (2,5-dichlorobenzamido) propoxy) benzene

(145) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(2,5-디클로로벤즈아미도)부티록시)벤젠(145) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (2,5-dichlorobenzamido) butyoxy) benzene

(146) 3,5-디에틸-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(2,4-비스(트리플루오로메틸)벤즈아미도)프로폭시)벤젠(146) 3,5-diethyl-1- (3,3-dichloro-2-propenyloxy) -4- (3- (2,4-bis (trifluoromethyl) benzamido) propoxy) benzene

(147) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(2-플루오로-4-(트리플루오로메틸)벤즈아미도)프로폭시)벤젠(147) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3- (2-fluoro-4- (trifluoromethyl) benzamido) propoxy )benzene

(148) 3,5-디에틸-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-(4-클로로-2-플루오로벤즈아미도)프로폭시)벤젠(148) 3,5-diethyl-1- (3,3-dichloro-2-propenyloxy) -4- (3- (4-chloro-2-fluorobenzamido) propoxy) benzene

하기의 화학식 (9)의 중간체의 제조예이다.The manufacture example of the intermediate of following General formula (9) is shown.

중간체 제조예 1Intermediate Preparation Example 1

중간체 화합물 1의 제조Preparation of Intermediate Compound 1

반응 용기를 30.5g의 4-히드록시페닐 벤조에이트, 21.6g의 탄산 칼륨, 20.8g의 1,1,3-트리클로로프로펜 및 100ml의 N,N-디메틸포름아미드로 충전시킨다. 실온에서 15시간 교반한 후, 반응 혼합물을 물에 쏟아붓고 150ml의 디에틸 에테르로 2회 추출한다. 에테르층을 취합하여 물로 세척하고 무수 황산 마그네슘으로 건조시킨 다음 농축하여, 조 생성물을 수득한다. 조 생성물을 실리카 겔 크로마토그래피하여, 44.1g의 4-(3,3-디클로로-2-프로페닐옥시)페닐 벤조에이트를 수득한다(수율 96%).The reaction vessel is charged with 30.5 g of 4-hydroxyphenyl benzoate, 21.6 g of potassium carbonate, 20.8 g of 1,1,3-trichloropropene and 100 ml of N, N-dimethylformamide. After 15 hours of stirring at room temperature, the reaction mixture is poured into water and extracted twice with 150 ml of diethyl ether. The ether layers are combined, washed with water, dried over anhydrous magnesium sulfate and concentrated to give the crude product. The crude product was subjected to silica gel chromatography to afford 44.1 g of 4- (3,3-dichloro-2-propenyloxy) phenyl benzoate (yield 96%).

반응 용기를 44.1g의 4-(3,3-디클로로-2-프로페닐옥시)페닐 벤조에이트와 400ml의 메탄올로 충전시키고, 30% 수산화 칼륨 수용액 33g을 빙냉하에 천천히 적가한다. 1시간 동안 교반한 후, 10% 염산을 첨가하여 혼합물을 약산성으로 만든 다음 염석하에 150ml의 디에틸 에테르로 2회 추출한다. 에테르층을 취합하여 물로 세척하고 무수 황산 마그네슘으로 건조시킨 다음 농축하여 조 생성물을 수득한다. 조 생성물을 실리카 겔 크로마토그래피하여, 26.0g의 4-(3,3-디클로로-2-프로페닐옥시)페놀을 수득한다(수율 87%).The reaction vessel is charged with 44.1 g of 4- (3,3-dichloro-2-propenyloxy) phenyl benzoate and 400 ml of methanol, and 33 g of an aqueous 30% potassium hydroxide solution is slowly added dropwise under ice cooling. After stirring for 1 hour, the mixture is made slightly acidic by addition of 10% hydrochloric acid and then extracted twice with 150 ml of diethyl ether under salting. The ether layers are combined, washed with water, dried over anhydrous magnesium sulfate and concentrated to give the crude product. The crude product is subjected to silica gel chromatography to give 26.0 g of 4- (3,3-dichloro-2-propenyloxy) phenol (yield 87%).

반응 용기를 26.0g의 4-(3,3-디클로로-2-프로페닐옥시)페놀과 500ml의 사염화 탄소로 충전시키고, 사염화 탄소 20ml에 녹인 tert-부틸히포클로라이트 27.1g을 빙냉 교반하에 천천히 적가한다. 24시간 동안 교반한 후, 반응 혼합물을 물에 쏟아붓고 유기층(사염화 탄소층)을 분리한다. 유기층을 취합하여 물로 세척하고 무수 황산 마그네슘으로 건조시킨 다음 농축하여 조 생성물을 수득한다. 조 생성물을 실리카 겔 크로마토그래피하여, 11.0g의 2,6-디클로로-4-(3,3-디클로로-2-프로페닐옥시)페놀을 수득한다(수율 32%, nD 22.51.5895).The reaction vessel was charged with 26.0 g of 4- (3,3-dichloro-2-propenyloxy) phenol and 500 ml of carbon tetrachloride, and 27.1 g of tert-butyl hypochlorite dissolved in 20 ml of carbon tetrachloride was slowly added dropwise with ice-cooled stirring. do. After stirring for 24 hours, the reaction mixture is poured into water and the organic layer (carbon tetrachloride layer) is separated. The organic layers are combined, washed with water, dried over anhydrous magnesium sulfate and concentrated to give the crude product. The crude product is subjected to silica gel chromatography to give 11.0 g of 2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenol (yield 32%, n D 22.5 1.5895).

하기는 화학식 (9)의 중간체의 일부 특정예를, 그의 화합물 번호 및 물리적 성질(측정될 경우)과 함께 기술하고 있다:The following describes some specific examples of intermediates of formula (9) with their compound numbers and physical properties (when measured):

1) 2,6-디클로로-4-(3,3-디클로로-2-프로페닐옥시)페놀1) 2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenol

1H-NMR(CDCl3/TMS) δ(ppm): 4.57(2H, d), 5.50(1H, brs), 6,11(1H, t), 6.85(2H, s) 1 H-NMR (CDCl 3 / TMS) δ (ppm): 4.57 (2H, d), 5.50 (1H, brs), 6,11 (1H, t), 6.85 (2H, s)

2) 2,6-디클로로-4-(3,3-디브로모-2-프로페닐옥시)페놀2) 2,6-dichloro-4- (3,3-dibromo-2-propenyloxy) phenol

3) 2-클로로--6-브로모-4-(3,3-디클로로-2-프로페닐옥시)페놀3) 2-chloro-6-bromo-4- (3,3-dichloro-2-propenyloxy) phenol

4) 2-클로로--6-브로모-4-(3,3-디브로모-2-프로페닐옥시)페놀4) 2-chloro-6-bromo-4- (3,3-dibromo-2-propenyloxy) phenol

5) 2,6-디브로모-4-(3,3-디클로로-2-프로페닐옥시)페놀5) 2,6-dibromo-4- (3,3-dichloro-2-propenyloxy) phenol

6) 2,6-디브로모-4-(3,3-디브로모-2-프로페닐옥시)페놀6) 2,6-dibromo-4- (3,3-dibromo-2-propenyloxy) phenol

7) 2,6-디메틸-4-(3,3-디클로로-2-프로페닐옥시)페놀7) 2,6-dimethyl-4- (3,3-dichloro-2-propenyloxy) phenol

8) 2,6-디메틸-4-(3,3-디브로모-2-프로페닐옥시)페놀8) 2,6-dimethyl-4- (3,3-dibromo-2-propenyloxy) phenol

9) 2-클로로-6-메틸-4-(3,3-디클로로-2-프로페닐옥시)페놀9) 2-chloro-6-methyl-4- (3,3-dichloro-2-propenyloxy) phenol

10) 2-클로로-6-메틸-4-(3,3-디브로모-2-프로페닐옥시)페놀.10) 2-chloro-6-methyl-4- (3,3-dibromo-2-propenyloxy) phenol.

하기는 화학식 (18)의 중간체의 제조예이다.The following is an example of the preparation of the intermediate of formula (18).

중간체 제조예 2Intermediate Preparation Example 2

중간체 화합물 12의 제조Preparation of Intermediate Compound 12

반응 용기를 10.6g의 1,3-디브로모프로판, 5.53g의 탄산 칼륨 및 100ml의 N,N-디메틸포름아미드로 충전시키고, 40ml의 N,N-디메틸포름아미드에 녹인 10.1g의 2,6-디클로로-4-(3,3-디클로로-2-프로페닐옥시)페놀 용액을 천천히 적가한다. 실온에서 24시간 동안 교반한 후, 반응 혼합물을 물에 쏟아붓고 150ml의 디에틸 에테르로 2회 추출한다. 에테르층을 취합하여 물로 세척하고 무수 황산 마그네슘으로 건조시킨 다음 농축하여, 조 생성물을 수득한다. 조 생성물을 실리카 겔 크로마토그래피하여, 11.1g의 3,5-디클로로-4-(3-브로모프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠을 수득한다(수율 77%).The reaction vessel was charged with 10.6 g of 1,3-dibromopropane, 5.53 g of potassium carbonate and 100 ml of N, N-dimethylformamide and dissolved in 40 ml of N, N-dimethylformamide in 10.1 g of 2, Slowly dropwise add the 6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenol solution. After stirring for 24 hours at room temperature, the reaction mixture is poured into water and extracted twice with 150 ml of diethyl ether. The ether layers are combined, washed with water, dried over anhydrous magnesium sulfate and concentrated to give the crude product. The crude product was subjected to silica gel chromatography to afford 11.1 g of 3,5-dichloro-4- (3-bromopropoxy) -1- (3,3-dichloro-2-propenyloxy) benzene (yield) 77%).

반응 용기를 11.1g의 3,5-디클로로-4-(3-브로모프로폭시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠, 3.31g의 벤조산, 3.90g의 탄산 칼륨 및 50ml의 N,N-디메틸포름아미드로 충전시킨다. 실온에서 24시간 동안 교반한 후, 반응 혼합물을 물에 쏟아붓고 150ml의 디에틸 에테르로 2회 추출한다. 에테르층을 취합하여 물로 세척하고 무수 염화 마그네슘으로 건조시킨 다음 농축하여, 조 생성물을 수득한다. 조 생성물을 실리카 겔 크로마토그래피하여, 11.6g의 3,5-디클로로-4-(3-벤조일옥시프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠을 수득한다(수율 95%).The reaction vessel was charged with 11.1 g of 3,5-dichloro-4- (3-bromopropoxy) -1- (3,3-dichloro-2-propenyloxy) benzene, 3.31 g of benzoic acid, 3.90 g of potassium carbonate And 50 ml of N, N-dimethylformamide. After stirring for 24 hours at room temperature, the reaction mixture is poured into water and extracted twice with 150 ml of diethyl ether. The ether layers are combined, washed with water, dried over anhydrous magnesium chloride and concentrated to give the crude product. The crude product was subjected to silica gel chromatography to give 11.6 g of 3,5-dichloro-4- (3-benzoyloxypropyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene (yield) 95%).

반응 용기를 11.6g의 3,5-디클로로-4-(3-벤조일옥시프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠, 15.2g의 10% 수산화 칼륨 용액 및 30ml의 메탄올로 충전시킨다. 실온에서 24시간 동안 교반한 후, 반응 혼합물을 농축한다.The reaction vessel was filled with 11.6 g of 3,5-dichloro-4- (3-benzoyloxypropyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene, 15.2 g of 10% potassium hydroxide solution and 30 ml Is charged with methanol. After stirring for 24 hours at room temperature, the reaction mixture is concentrated.

이 농축물에 물을 쏟아붓고, 상기 혼합물을 150ml의 디에틸 에테르로 2회 추출한다. 에테르층을 취합하여 물로 세척하고 무수 황산 마그네슘으로 건조시킨 다음 농축하여, 조 생성물을 수득한다. 조 생성물을 실리카 겔 크로마토그래피하여, 7,41g의 3-(2,6-디클로로-4-(3,3-디클로로-2-프로페닐옥시)페녹시)-프로파놀을 수득한다(수율 83%, m.p. 56.6℃).Water is poured into this concentrate and the mixture is extracted twice with 150 ml of diethyl ether. The ether layers are combined, washed with water, dried over anhydrous magnesium sulfate and concentrated to give the crude product. The crude product was subjected to silica gel chromatography to afford 7,41 g of 3- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) -propanol (yield 83%). , mp 56.6 ° C.).

하기는 화학식 (18)의 중간체의 일부 특정예를, 그의 화합물 번호 및 물리적 성질(측정될 경우)과 함께 기술하고 있다:The following describes some specific examples of the intermediates of formula (18) with their compound numbers and physical properties (when measured):

11) 2-(2,6-디클로로-4-(3,3-디클로로-2-프로페닐옥시)페녹시)에탄올11) 2- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) ethanol

12) 2-(2,6-디클로로-4-(3,3-디클로로-2-프로페닐옥시)페녹시)-1-프로판올12) 2- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) -1-propanol

m.p. 56.6℃m.p. 56.6 ℃

13) 4-(2,6-디클로로-4-(3,3-디클로로-2-프로페닐옥시)페녹시)-1-부탄올13) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) -1-butanol

14) 5-(2,6-디클로로-4-(3,3-디클로로-2-프로페닐옥시)페녹시)-1-펜탄올14) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) -1-pentanol

15) 2-(2,6-디클로로-4-(3,3-디클로로-2-프로페닐옥시)페녹시)-1-에탄티올15) 2- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) -1-ethanethiol

16) 3-(2,6-디클로로-4-(3,3-디클로로-2-프로페닐옥시)페녹시)-1-프로판티올16) 3- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) -1-propanethiol

17) 4-(2,6-디클로로-4-(3,3-디클로로-2-프로페닐옥시)페녹시)-1-부탄티올17) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) -1-butanethiol

18) 5-(2,6-디클로로-4-(3,3-디클로로-2-프로페닐옥시)페녹시)-1-펜탄티올.18) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) -1-pentanethiol.

하기는 화학식 (12)의 중간체의 제조예이다.The following is an example of the preparation of the intermediate of formula (12).

중간체 제조예 3Intermediate Preparation Example 3

중간체 화합물 21의 제조Preparation of Intermediate Compound 21

반응 용기를 4.09g의 3,5-디클로로-4-(3-브로모프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠, 2.41g의 포타슘 프탈이미드 및 30ml의 N,N-디메틸포름아미드로 충전시킨다. 실온에서 24시간 동안 교반한 후, 반응 혼합물을 물에 쏟아붓고 150ML의 클로로포름으로 2회 추출한다. 클로로포름층을 취합하여, 희석 염산 및 희석 수산화 나트륨 수용액으로 세척하고, 무수 황산 마그네슘으로 건조시킨 다음, 농축하여, 4.67g의 3,5-디클로로-4-(3-프탈이미도프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠 조 생성물을 수득한다(수율 98%).The reaction vessel was prepared with 4.09 g of 3,5-dichloro-4- (3-bromopropyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene, 2.41 g of potassium phthalimide and 30 ml Charge with N, N-dimethylformamide. After stirring for 24 hours at room temperature, the reaction mixture is poured into water and extracted twice with 150 ml of chloroform. The chloroform layers are combined, washed with dilute hydrochloric acid and dilute sodium hydroxide aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated to 4.67 g of 3,5-dichloro-4- (3-phthalimidopropyloxy) -1- Obtained (3,3-dichloro-2-propenyloxy) benzene crude product (yield 98%).

반응 용기를 4.67g의 3,5-디클로로-4-(3-프탈이미도프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠 조 생성물, 0.55g의 히드라진 일수화물 및 200ml의 에탄올로 충전시킨다. 환류하에 2시간 동안 가열한 후, 진한 염산을 첨가하여 반응 혼합물을 약산성으로 만든 다음 환류하에 1시간 동안 더 가열한다. 침전된 고체를 여과로 취합하고 여액은 농축한다. 농축물에 물을 쏟아붓고 150ml의 클로로포름으로 2회 추출한다. 클로로포름층을 취합하여 물로 세척하고 무수 황산 마그네슘으로 건조시킨 다음 농축하여 조 생성물을 수득한다. 조 생성물을 실리카 겔 크로마토그래피하여, 2.4g의 3,5-디클로로-4-(3-아미노프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠을 수득한다:4.67 g of 3,5-dichloro-4- (3-phthalimidopropyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene crude product, 0.55 g of hydrazine monohydrate and 200 ml Is filled with ethanol. After 2 hours of heating under reflux, the reaction mixture is made slightly acidic by adding concentrated hydrochloric acid and then further heated under reflux for 1 hour. The precipitated solid is collected by filtration and the filtrate is concentrated. Pour water into the concentrate and extract twice with 150 ml of chloroform. The chloroform layers are combined, washed with water, dried over anhydrous magnesium sulfate and concentrated to give the crude product. The crude product is subjected to silica gel chromatography to give 2.4 g of 3,5-dichloro-4- (3-aminopropyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene:

(수율 71%, nD 23.51.5672).(Yield 71%, n D 23.5 1.5 672).

중간체 제조예 4Intermediate Preparation Example 4

중간체 화합물 23의 제조Preparation of Intermediate Compound 23

9.1g의 2,6-디클로로-4-(3,3-디클로로-2-프로페닐옥시)페놀, 8.9g의 N-(4-브로모에틸)프탈이미드, 4.4g의 탄산 칼륨 및 100ml의 N,N-디메틸포름아미드의 혼합물을 실온에서 24시간 동안 교반한다. 반응 혼합물을 얼음물에 쏟아붓고 10%의 염산을 첨가하여 약산성으로 만들고 난 후, 200ml의 에틸 아세테이트를 첨가하여 추출한다. 에틸 아세테이트층을 연속적으로 10% 염산 및 포화 염수로 세척하고 무수 황산 마그네슘으로 건조하고 농축하여 조 결정을 수득한다. 상기 조 결정을 n-헥산으로 세척하고 감압 건조하여, 14.5g의 3,5-디클로로-4-(4-프탈이미도부틸옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠을 수득한다(수율 94%).9.1 g 2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenol, 8.9 g N- (4-bromoethyl) phthalimide, 4.4 g potassium carbonate and 100 ml The mixture of N, N-dimethylformamide is stirred at room temperature for 24 hours. The reaction mixture is poured into ice water and made weakly acidic by addition of 10% hydrochloric acid, followed by extraction with 200 ml ethyl acetate. The ethyl acetate layer was washed successively with 10% hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate and concentrated to give crude crystals. The crude crystals were washed with n-hexane and dried under reduced pressure to obtain 14.5 g of 3,5-dichloro-4- (4-phthalimidobutyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene Obtained (yield 94%).

14.5g의 3,5-디클로로-4-(4-프탈이미도부틸옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠, 1.73ml의 히드라진 일수화물 및 100ml의 에탄올의 혼합물을 환류하에 4시간 동안 가열한다. 진한 염산을 첨가하여 반응 혼합물을 약산성으로 만든 다음 환류하에 1시간 동안 더 가열한다. 반응 혼합물의 온도를 실온으로 낮춘 후, 침전된 고체를 여과로 모으고 여액은 농축하여 잔류물을 수득한다.A mixture of 14.5 g of 3,5-dichloro-4- (4-phthalimidobutyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene, 1.73 ml of hydrazine monohydrate and 100 ml of ethanol Heat at reflux for 4 hours. The reaction mixture is made slightly acidic by addition of concentrated hydrochloric acid and then heated under reflux for 1 hour. After lowering the temperature of the reaction mixture to room temperature, the precipitated solids are collected by filtration and the filtrate is concentrated to give a residue.

잔류물에 100ml의 에탄올에 녹인 2.1g의 수산화 칼륨 용액을 첨가하고, 침전된 고체를 여과로 모으고 여액은 농축하여 잔류물을 수득한다. 잔류물에 100ml의 디에틸 에테르를 첨가하여 용해시키고, 용액을 무수 황산 마그네슘으로 건조시키고 농축하여, 7.51g의 3,5-디클로로-4-(4-아미노부틸옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠을 수득한다(수율 71%, nD 23.51.5672).To the residue is added 2.1 g of potassium hydroxide solution dissolved in 100 ml of ethanol, the precipitated solid is collected by filtration and the filtrate is concentrated to give a residue. To the residue was dissolved by adding 100 ml of diethyl ether, and the solution was dried over anhydrous magnesium sulfate and concentrated to give 7.51 g of 3,5-dichloro-4- (4-aminobutyloxy) -1- (3,3 -Dichloro-2-propenyloxy) benzene is obtained (yield 71%, n D 23.5 1.5672).

중간체 제조예 5Intermediate Preparation Example 5

중간체 화합물 60의 제조Preparation of Intermediate Compound 60

1.0g의 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-브로모부틸옥시)벤젠, 메탈아민의 40% 메탄올 용액 4ml, 0.33g의 탄산 칼륨 및 N,N-디메틸포름아미드의 혼합물을 실온에서 24시간 동안 교반한다. 반응 혼합물에 100ml의 포화 탄산수소 나트륨 용액을 첨가하고 난 후, 100ml의 에틸 아세테이트로 추출한다. 에틸 아세테이트층을 연속적으로 100ml의 포화 탄산수소 나트륨 및 포화 염수로 세척하고, 무수 황산 마그네슘으로 건조시키고 농축하여, 0.80g의 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-(메틸아미노)부틸옥시)벤젠을 수득한다(수율 89%, nD 26.01.5545).1.0 g of 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4-bromobutyloxy) benzene, 4 ml of 40% methanol solution of metalamine, 0.33 g of carbonic acid The mixture of potassium and N, N-dimethylformamide is stirred at room temperature for 24 hours. To the reaction mixture is added 100 ml of saturated sodium bicarbonate solution and then extracted with 100 ml of ethyl acetate. The ethyl acetate layer was washed successively with 100 ml of saturated sodium bicarbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated to give 0.80 g of 3,5-dichloro-1- (3,3-dichloro-2-propenyl). Oxy) -4- (4- (methylamino) butyloxy) benzene is obtained (yield 89%, n D 26.0 1.5545).

하기는 화학식 (3) 또는 (12)의 중간체의 일부 특정예를, 그의 화합물 번호 및 물리적 성질(측정될 경우)과 함께 기술하고 있다:The following describes some specific examples of the intermediates of formula (3) or (12), with their compound numbers and physical properties (when measured):

19) 3,5-디클로로-4-(2-아미노에톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠19) 3,5-dichloro-4- (2-aminoethoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

nD 25.01.5784n D 25.0 1.5784

20) 3,5-디클로로-4-(2-아미노에톡시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠20) 3,5-dichloro-4- (2-aminoethoxy) -1- (3,3-dibromo-2-propenyloxy) benzene

21) 3,5-디클로로-4-(3-아미노프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠nD 25.01.578421) 3,5-dichloro-4- (3-aminopropyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene n D 25.0 1.5784

22) 3,5-디클로로-4-(3-아미노프로필옥시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠22) 3,5-dichloro-4- (3-aminopropyloxy) -1- (3,3-dibromo-2-propenyloxy) benzene

23) 3,5-디클로로-4-(3-아미노부틸옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠nD 24.51.572223) 3,5-dichloro-4- (3-aminobutyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene n D 24.5 1.5722

24) 3,5-디클로로-4-(2-아미노부틸옥시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠24) 3,5-dichloro-4- (2-aminobutyloxy) -1- (3,3-dibromo-2-propenyloxy) benzene

25) 3,5-디클로로-4-(5-아미노펜틸옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠25) 3,5-dichloro-4- (5-aminopentyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene

26) 3,5-디클로로-4-(5-아미노펜틸옥시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠26) 3,5-dichloro-4- (5-aminopentyloxy) -1- (3,3-dibromo-2-propenyloxy) benzene

27) 3,5-디브로모-4-(2-아미노에톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠27) 3,5-dibromo-4- (2-aminoethoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

28) 3,5-디브로모-4-(2-아미노에톡시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠28) 3,5-dibromo-4- (2-aminoethoxy) -1- (3,3-dibromo-2-propenyloxy) benzene

29) 3,5-디브로모-4-(3-아미노프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠29) 3,5-dibromo-4- (3-aminopropyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene

30) 3,5-디브로모-4-(3-아미노프로필옥시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠30) 3,5-dibromo-4- (3-aminopropyloxy) -1- (3,3-dibromo-2-propenyloxy) benzene

31) 3,5-디브로모-4-(4-아미노부틸옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠31) 3,5-dibromo-4- (4-aminobutyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene

32) 3,5-디브로모-4-(4-아미노부틸옥시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠32) 3,5-dibromo-4- (4-aminobutyloxy) -1- (3,3-dibromo-2-propenyloxy) benzene

33) 3,5-디브로모-4-(5-아미노펜틸옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠33) 3,5-dibromo-4- (5-aminopentyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene

34) 3,5-디브로모-4-(4-아미노부틸옥시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠34) 3,5-dibromo-4- (4-aminobutyloxy) -1- (3,3-dibromo-2-propenyloxy) benzene

35) 3,5-디메틸-4-(2-아미노에톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠35) 3,5-dimethyl-4- (2-aminoethoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

36) 3,5-디메틸-4-(2-아미노에톡시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠36) 3,5-dimethyl-4- (2-aminoethoxy) -1- (3,3-dibromo-2-propenyloxy) benzene

37) 3,5-디메틸-4-(3-아미노프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠37) 3,5-dimethyl-4- (3-aminopropyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene

38) 3,5-디메틸-4-(3-아미노프로필옥시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠38) 3,5-dimethyl-4- (3-aminopropyloxy) -1- (3,3-dibromo-2-propenyloxy) benzene

39) 3,5-디메틸-4-(4-아미노부틸옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠39) 3,5-dimethyl-4- (4-aminobutyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene

40) 3,5-디메틸-4-(4-아미노부틸옥시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠40) 3,5-dimethyl-4- (4-aminobutyloxy) -1- (3,3-dibromo-2-propenyloxy) benzene

41) 3,5-디메틸-4-(5-아미노펜틸옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠41) 3,5-dimethyl-4- (5-aminopentyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene

42) 3,5-디메틸-4-(5-아미노펜틸옥시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠42) 3,5-dimethyl-4- (5-aminopentyloxy) -1- (3,3-dibromo-2-propenyloxy) benzene

43) 3-클로로-5-메틸-4-(2-아미노에톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠43) 3-chloro-5-methyl-4- (2-aminoethoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

44) 3-클로로-5-메틸-4-(2-아미노에톡시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠44) 3-chloro-5-methyl-4- (2-aminoethoxy) -1- (3,3-dibromo-2-propenyloxy) benzene

45) 3-클로로-5-메틸-4-(3-아미노프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠45) 3-chloro-5-methyl-4- (3-aminopropyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene

46) 3-클로로-5-메틸-4-(3-아미노프로필옥시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠46) 3-chloro-5-methyl-4- (3-aminopropyloxy) -1- (3,3-dibromo-2-propenyloxy) benzene

47) 3-클로로-5-메틸-4-(3-아미노부틸옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠47) 3-chloro-5-methyl-4- (3-aminobutyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene

48) 3-클로로-5-메틸-4-(4-아미노부틸옥시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠48) 3-chloro-5-methyl-4- (4-aminobutyloxy) -1- (3,3-dibromo-2-propenyloxy) benzene

49) 3-클로로-5-메틸-4-(5-아미노펜틸옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠49) 3-chloro-5-methyl-4- (5-aminopentyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene

50) 3-클로로-5-메틸-4-(5-아미노펜틸옥시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠50) 3-chloro-5-methyl-4- (5-aminopentyloxy) -1- (3,3-dibromo-2-propenyloxy) benzene

51) 3-에틸-5-메틸-4-(2-아미노에톡시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠51) 3-ethyl-5-methyl-4- (2-aminoethoxy) -1- (3,3-dichloro-2-propenyloxy) benzene

52) 3-에틸-5-메틸-4-(2-아미노에톡시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠52) 3-ethyl-5-methyl-4- (2-aminoethoxy) -1- (3,3-dibromo-2-propenyloxy) benzene

53) 3-에틸-5-메틸-4-(3-아미노프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠53) 3-ethyl-5-methyl-4- (3-aminopropyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene

54) 3-에틸-5-메틸-4-(3-아미노프로필옥시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠54) 3-ethyl-5-methyl-4- (3-aminopropyloxy) -1- (3,3-dibromo-2-propenyloxy) benzene

55) 3-에틸-5-메틸-4-(4-아미노부틸옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠55) 3-ethyl-5-methyl-4- (4-aminobutyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene

56) 3-에틸-5-메틸-4-(4-아미노부틸옥시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠56) 3-ethyl-5-methyl-4- (4-aminobutyloxy) -1- (3,3-dibromo-2-propenyloxy) benzene

57) 3-에틸-5-메틸-4-(5-아미노펜틸옥시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠57) 3-ethyl-5-methyl-4- (5-aminopentyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene

58) 3-에틸-5-메틸-4-(5-아미노펜틸옥시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠58) 3-ethyl-5-methyl-4- (5-aminopentyloxy) -1- (3,3-dibromo-2-propenyloxy) benzene

59) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(3-메틸아미노)프로필옥시)벤젠nD 26.01.561859) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (3-methylamino) propyloxy) benzenen D 26.0 1.5618

59) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-메틸아미노)부틸옥시)벤젠nD 26.01.554559) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4-methylamino) butyloxy) benzene n D 26.0 1.5545

59) 3,5-디클로로-1-(3,3-디클로로-2-프로페닐옥시)-4-(4-이소프로필아미노)부틸옥시)벤젠nD 24.51.5355.59) 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4-isopropylamino) butyloxy) benzenen D 24.5 1.5355.

하기는 화학식 (3) 또는 (12)의 중간체의 제조예이다.The following is an example of the preparation of the intermediate of the formula (3) or (12).

중간체 제조예 6Intermediate Preparation Example 6

중간체 화합물 62의 제조Preparation of Intermediate Compound 62

반응 용기를 2.02g의 2,6-디클로로-4-(3,3-디클로로-2-프로페닐옥시)페놀, 1.56g의 에틸 3-브로모부티레이트, 11.1g의 탄산 칼륨 및 20ml의 N,N-디메틸 포름아미드로 충전시킨다. 실온에서 12시간 동안 교반한 후, 반응 혼합물을 물에 쏟아붓고 50ml의 에틸 아세테이트로 2회 추출한다. 에틸 아세테이트층을 취합하여 물로 세척하고 무수 황산 마그네슘으로 건조하고 농축하여 조 생성물을 수득한다. 상기 조 생성물을 실리카 겔 크로마토그래피하여, 2.54g의 에틸 2,6-디클로로-4-(3,3-디클로로-2-프로페닐옥시)페녹시부티레이트를 수득한다(수율 90%).The reaction vessel was prepared with 2.02 g of 2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenol, 1.56 g of ethyl 3-bromobutyrate, 11.1 g of potassium carbonate and 20 ml of N, N Fill with dimethyl formamide. After stirring for 12 hours at room temperature, the reaction mixture is poured into water and extracted twice with 50 ml of ethyl acetate. The ethyl acetate layer is combined, washed with water, dried over anhydrous magnesium sulfate and concentrated to give the crude product. The crude product was subjected to silica gel chromatography to afford 2.54 g of ethyl 2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxybutyrate (yield 90%).

반응 용기를 2.54g의 에틸 2.6-디클로로-4-(3,3-디클로로-2-프로페닐옥시)페녹시부티레이트, 4.0g의 10% 수산화 칼륨 수용액 및 50ml의 메탄올로 충전시킨다. 실온에서 24시간 동안 교반한 후 반응 혼합물을 농축한다. 그 다음 50ml의 에틸 아세테이트를 상기 혼합물에 쏟아붓고, 혼합물을 50ml의 5% 탄산수소 나트륨 수용액으로 2회 추출한다. 물층을 취합하고, 진한 염산을 첨가하여 반응 혼합물을 약산성으로 만든다. 침전된 결정을 50ml의 디에틸 에테르로 2회 추출한다. 에테르층을 취합하여 물로 세척하고 무수 황산 마그네슘으로 건조하고 농축하여, 2.11g의 4-(2,6-디클로로-4-(3,3-디클로로-2-프로페닐옥시)페녹시)부티르산 수득한다(수율 90%, m.p. 80.9℃).The reaction vessel is charged with 2.54 g of ethyl 2.6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxybutyrate, 4.0 g of 10% aqueous potassium hydroxide solution and 50 ml of methanol. After stirring for 24 hours at room temperature the reaction mixture is concentrated. 50 ml of ethyl acetate is then poured into the mixture and the mixture is extracted twice with 50 ml of 5% aqueous sodium hydrogen carbonate solution. The aqueous layers are combined and concentrated hydrochloric acid is added to make the reaction mixture slightly acidic. The precipitated crystals are extracted twice with 50 ml of diethyl ether. The ether layers are combined, washed with water, dried over anhydrous magnesium sulfate and concentrated to give 2.11 g of 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyric acid. (Yield 90%, mp 80.9 ° C.).

하기는 화학식 (3) 또는 (12)의 중간체의 일부 특정예를, 그의 화합물 번호 및 물리적 성질)측정될 경우)과 함께 기술하고 있다:The following describes some specific examples of intermediates of formula (3) or (12) with their compound numbers and physical properties when measured):

62) 4-(2,6-디클로로-4-(3,3-디클로로-2-프로페닐옥시)페녹시)부티르산62) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyric acid

m.p. 80.9℃m.p. 80.9 ℃

63) 4-(2,6-디클로로-4-(3,3-디브로모-2-프로페닐옥시)페녹시)부티르산63) 4- (2,6-dichloro-4- (3,3-dibromo-2-propenyloxy) phenoxy) butyric acid

64) 5-(2,6-디클로로-4-(3,3-디클로로-2-프로페닐옥시)페녹시)발레르산64) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) valeric acid

m.p. 75.7℃m.p. 75.7 ℃

65) 5-(2,6-디클로로-4-(3,3-디브로모-2-프로페닐옥시)페녹시)발레르산65) 5- (2,6-dichloro-4- (3,3-dibromo-2-propenyloxy) phenoxy) valeric acid

66) 4-(2,6-디브로모-4-(3,3-디클로로-2-프로페닐옥시)페녹시)부티르산66) 4- (2,6-dibromo-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyric acid

67) 4-(2,6-디브로모-4-(3,3-디브로모-2-프로페닐옥시)페녹시)부티르산67) 4- (2,6-dibromo-4- (3,3-dibromo-2-propenyloxy) phenoxy) butyric acid

68) 5-(2,6-디브로모-4-(3,3-디클로로-2-프로페닐옥시)페녹시)발레르산68) 5- (2,6-dibromo-4- (3,3-dichloro-2-propenyloxy) phenoxy) valeric acid

69) 5-(2,6-디브로모-4-(3,3-디브로모-2-프로페닐옥시)페녹시)발레르산69) 5- (2,6-dibromo-4- (3,3-dibromo-2-propenyloxy) phenoxy) valeric acid

70) 4-(2,6-디메틸-4-(3,3-디클로로-2-프로페닐옥시)페녹시)부티르산70) 4- (2,6-dimethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyric acid

71) 4-(2,6-디메틸-4-(3,3-디브로모-2-프로페닐옥시)페녹시)부티르산71) 4- (2,6-dimethyl-4- (3,3-dibromo-2-propenyloxy) phenoxy) butyric acid

72) 5-(2,6-디메틸-4-(3,3-디클로로-2-프로페닐옥시)페녹시)발레르산72) 5- (2,6-dimethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) valeric acid

73) 5-(2,6-디메틸-4-(3,3-디브로모-2-프로페닐옥시)페녹시)발레르산73) 5- (2,6-dimethyl-4- (3,3-dibromo-2-propenyloxy) phenoxy) valeric acid

74) 4-(2-클로로-6-메틸-4-(3,3-디클로로-2-프로페닐옥시)페녹시)부티르산74) 4- (2-chloro-6-methyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyric acid

75) 4-(2-클로로-6-메틸-4-(3,3-디브로모-2-프로페닐옥시)페녹시)부티르산75) 4- (2-chloro-6-methyl-4- (3,3-dibromo-2-propenyloxy) phenoxy) butyric acid

76) 5-(2-클로로-6-메틸-4-(3,3-디클로로-2-프로페닐옥시)페녹시)발레르산76) 5- (2-chloro-6-methyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) valeric acid

77) 5-(2-클로로-6-메틸-4-(3,3-디브로모-2-프로페닐옥시)페녹시)발레르산77) 5- (2-chloro-6-methyl-4- (3,3-dibromo-2-propenyloxy) phenoxy) valeric acid

78) 4-(2-에틸-6-메틸-4-(3,3-디클로로-2-프로페닐옥시)페녹시)부티르산78) 4- (2-ethyl-6-methyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyric acid

79) 4-(2-에틸-6-메틸-4-(3,3-디브로모-2-프로페닐옥시)페녹시)부티르산79) 4- (2-ethyl-6-methyl-4- (3,3-dibromo-2-propenyloxy) phenoxy) butyric acid

80) 5-(2-에틸-6-메틸-4-(3,3-디클로로-2-프로페닐옥시)페녹시)발레르산80) 5- (2-ethyl-6-methyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) valeric acid

81) 5-(2-에틸-6-메틸-4-(3,3-디브로모-2-프로페닐옥시)페녹시)발레르산.81) 5- (2-ethyl-6-methyl-4- (3,3-dibromo-2-propenyloxy) phenoxy) valeric acid.

하기는 화학식 (4) 또는 (5)의 중간체의 제조예이다.The following is an example of the preparation of the intermediate of the formula (4) or (5).

중간체 제조예 7Intermediate Preparation Example 7

중간체 화합물 84의 제조Preparation of Intermediate Compound 84

반응 용기를 7.51g의 3-아미노-1-프로파놀, 2.53g의 트리에틸아민 및 50ml의 디클로로메탄으로 충전시키고, 5.21g의 4-트리플루오로메틸벤조일 클로라이드를 빙냉하에 천천히 적가한다. 실온에서 6시간 동안 교반한 후, 반응 혼합물을 희석 염산 및 물로 연속적으로 세척하고 무수 황산 마그네슘으로 건조하고 농축하여, 5.25g의 3-(4-트리플루오로메틸벤즈아미도)프로판-1-올을 수득한다(수율 85%).The reaction vessel is charged with 7.51 g of 3-amino-1-propanol, 2.53 g of triethylamine and 50 ml of dichloromethane, and 5.21 g of 4-trifluoromethylbenzoyl chloride is slowly added dropwise under ice-cooling. After stirring for 6 hours at room temperature, the reaction mixture was washed successively with dilute hydrochloric acid and water, dried over anhydrous magnesium sulfate and concentrated to give 5.25 g of 3- (4-trifluoromethylbenzamido) propan-1-ol Obtained (yield 85%).

반응 용기를 5.25g(21.2mmol)의 3-(4-트리플루오로메틸벤즈아미도)프로판-1-올, 5.72g(21.2mmol)의 4-벤질옥시-2,6-디클로로페놀, 5.29g(20.2mmol)의 트리페닐포스핀 및 100ml의 테트라히드로푸란으로 충전시키고, 20ml의 테트라히드로푸란에 녹인 4.08g(20.2mmol)의 디이소프로필 아조디카르복실레이트 용액을 교반하에서 적가한다. 실온에서 12시간 동안 교반한 후 반응 혼합물을 농축하고 잔류물을 실리카 겔 크로마토그래피하여, 1-벤질옥시-3,5-디클로로-4-(3-(4-트리플루오로메틸벤즈아미도)프로필옥시)벤젠을 수득한다.5.25 g (21.2 mmol) 3- (4-trifluoromethylbenzamido) propan-1-ol, 5.72 g (21.2 mmol) 4-benzyloxy-2,6-dichlorophenol, 5.29 g Charged with (20.2 mmol) triphenylphosphine and 100 ml tetrahydrofuran, and 4.08 g (20.2 mmol) diisopropyl azodicarboxylate solution dissolved in 20 ml tetrahydrofuran are added dropwise under stirring. After stirring for 12 hours at room temperature the reaction mixture was concentrated and the residue was subjected to silica gel chromatography to give 1-benzyloxy-3,5-dichloro-4- (3- (4-trifluoromethylbenzamido) propyl Oxy) benzene is obtained.

1-벤질옥시-3,5-디클로로-4-(3-(4-트리플루오로메틸벤즈아미도)프로필옥시)벤젠을 에틸 아세테이트에 녹이고, 이것을 반응 용기에 충전시키고, 용기내의 공기를 질소 기체로 대체한다. 촉매량의 10% 팔라듐/탄소를 첨가하고, 용기내의 질소 기체를 수소 기체로 대체한 다음, 실온에서 24시간 동안 격력하게 교반한다.Dissolve 1-benzyloxy-3,5-dichloro-4- (3- (4-trifluoromethylbenzamido) propyloxy) benzene in ethyl acetate, charge it to a reaction vessel, and charge the air in the vessel with nitrogen gas. Replace with A catalytic amount of 10% palladium / carbon is added and the nitrogen gas in the vessel is replaced with hydrogen gas and then vigorously stirred at room temperature for 24 hours.

용기내의 수소 기체를 질소 기체로 대체시키고 나서, 반응 혼합물을 세라이트(cerite)로 여과하고 여액을 농축하여, 3,5-디클로로-4-(3-(4-트리플루오로메틸벤즈아미도)프로필옥시)페놀을 수득한다.The hydrogen gas in the vessel was replaced with nitrogen gas, then the reaction mixture was filtered through cerite and the filtrate was concentrated to give 3,5-dichloro-4- (3- (4-trifluoromethylbenzamido) Propyloxy) phenol is obtained.

중간체 제조예 8Intermediate Preparation Example 8

중간체 화합물 120의 제조Preparation of Intermediate Compound 120

27g의 2-메틸-6-메틸아닐린, 36ml의 농축 황산 및 100ml의 물의 혼합물에, 50ml의 물에 녹인 16.,1g의 아질산 나트륨 용액을 적가하고, 0℃ 내지 5℃의 온도에서 교반한다. 적가가 끝난 후, 150g의 냉각수, 1.5g의 우레아 및 150g의 얼음을 첨가한다.To a mixture of 27 g 2-methyl-6-methylaniline, 36 ml concentrated sulfuric acid and 100 ml of water, 16., 1 g of sodium nitrite solution dissolved in 50 ml of water is added dropwise and stirred at a temperature of 0 ° C to 5 ° C. After the dropping, 150 g of coolant, 1.5 g of urea and 150 g of ice are added.

상기 수용액을 교반하에 135℃에서 가열하고 있는 100ml의 황산, 100ml의 물 및 150g의 황산 나트륨의 혼합물 용액에 적가한다. 적가와 동시에 증기 증류를 수행한다. 적가가 종결된 후, 증기 증류에 의해 수득된 수용액을 염화 나트륨으로 염석하고 무수 황산 마그네슘으로 건조시키고 농축하여 조 생성물을 수득한다. 조 생성물을 실리카 겔 크로마토그래피하여, 16g의 2-에틸-6-메틸 페놀을 수득한다(수율 59%).The aqueous solution is added dropwise to a mixture solution of 100 ml of sulfuric acid, 100 ml of water and 150 g of sodium sulfate, which is heated at 135 ° C. under stirring. Perform steam distillation simultaneously with the dropwise addition. After completion of the dropwise addition, the aqueous solution obtained by steam distillation is salted with sodium chloride, dried over anhydrous magnesium sulfate and concentrated to give a crude product. The crude product is subjected to silica gel chromatography to give 16 g of 2-ethyl-6-methyl phenol (yield 59%).

그리고 나서, 16g의 2-에틸-6-메틸페놀을 200ml의 클로로포름에 녹이고 0℃에서 교반하고, 이 용액에 56.6g의 테트라부틸암모늄 트리브로마이드를 소량씩 첨가한다. 실온에서 1시간 동안 교반한 후, 감압 증류하에 용매를 제거한다. 잔류물을 300ml의 디에틸 에테르에 녹이고, 10% 염산 및 물로 연속적으로 세척하고 무수 황산 마그네슘으로 건조하고 농축하여 조 생성물을 수득한다.Then, 16 g of 2-ethyl-6-methylphenol is dissolved in 200 ml of chloroform and stirred at 0 ° C., and 56.6 g of tetrabutylammonium tribromide is added to this solution in small portions. After stirring for 1 hour at room temperature, the solvent is removed under reduced pressure distillation. The residue is taken up in 300 ml of diethyl ether, washed successively with 10% hydrochloric acid and water, dried over anhydrous magnesium sulfate and concentrated to give the crude product.

조 생성물을 실리카 겔 크로마토그래피하여, 23g의 4-브로모-2-에틸-6-메틸페놀을 수득한다(수율 92%).The crude product is subjected to silica gel chromatography to give 23 g of 4-bromo-2-ethyl-6-methylphenol (yield 92%).

26g의 4-브로모-2-에틸-6-메틸페놀, 24.8g의 벤질 브로마이드 및 200ml의 N,N-디메틸포름아미드의 혼합물에, 0.68g의 탄산 칼륨을 첨가하고, 실온에서 교반한다. 실온에서 24시간 동안 교반한 후, 반응 혼합물을 얼음물에 쏟아붓고, 500ml의 디에틸 에테르로 2회 추출한다. 디에틸 에테르층을 취합하여 물로 세척하고 무수 황산 마그네슘으로 건조한 다음 농축하여, 조 생성물을 수득한다. 상기 조 생성물을 실리카 겔 크로마토그래피하여, 35.6g의 4-브로모-2-에틸-6-1-벤질옥시벤젠을 수득한다(수율 97%).To a mixture of 26 g of 4-bromo-2-ethyl-6-methylphenol, 24.8 g of benzyl bromide, and 200 ml of N, N-dimethylformamide, 0.68 g of potassium carbonate is added and stirred at room temperature. After stirring for 24 hours at room temperature, the reaction mixture is poured into iced water and extracted twice with 500 ml of diethyl ether. The diethyl ether layer was combined, washed with water, dried over anhydrous magnesium sulfate and concentrated to give the crude product. The crude product was subjected to silica gel chromatography to give 35.6 g of 4-bromo-2-ethyl-6-1-benzyloxybenzene (yield 97%).

그 다음 35.6g의 4-브로모-2-에틸-6-1-벤질옥시벤젠을 250ml의 테트라히드로푸란과 69ml의 n-부틸 리튬 용액(헥산중:1.69mol/liter)에 녹이고, -70℃에서 교반한다. 추가로 -70℃에서 2시간 동안 교반한 후, 50ml의 테트라히드로푸란에 녹인 12.1g의 트리메톡시보론 용액을 반응 혼합물에 적가한다. 적가가 끝난 후, 반응 혼합물을 실온으로 되돌리고, 1시간 동안 교반한 다음 얼음물에 쏟아붓는다. 10% 염산을 첨가하여 혼합물을 약산성으로 만든 다음 500ml의 디에틸 에테르로 추출한다. 에테르층을 취합하여 물로 세척하고 무수 황산 마그네슘으로 건조시키고 농축하여 잔류물을 수득한다. 상기 잔류물에 120ml의 톨루엔과 33ml의 30% 과산화수소수를 적가하고 70℃에서 가열 교반한다. 환류하에 1시간 동안 가열한 후, 반응 혼합물의 온도를 실온으로 하고, 물로 1회, 10% 황산 암모늄 철(ferrous ammonium sulfate)로 2회, 그리고 물로 1회 세척한다. 톨루엔층을 무수 황산 마그네슘으로 건조시키고 농축하여 조 생성물을 수득한다. 조 생성물을 실리카 겔 크로마토그래피하여, 26.2g의 3-메틸-4-벤질옥시-5-메틸페놀을 수득한다(수율 93%).35.6 g of 4-bromo-2-ethyl-6-1-benzyloxybenzene was then dissolved in 250 ml of tetrahydrofuran and 69 ml of n-butyl lithium solution (1.69 mol / liter in hexane), and -70 ° C. Stir in After further stirring at −70 ° C. for 2 hours, 12.1 g of trimethoxyboron solution dissolved in 50 ml of tetrahydrofuran is added dropwise to the reaction mixture. After the dropwise addition, the reaction mixture is returned to room temperature, stirred for 1 hour and then poured into ice water. The mixture is made slightly acidic by adding 10% hydrochloric acid and then extracted with 500 ml of diethyl ether. The ether layers are combined, washed with water, dried over anhydrous magnesium sulfate and concentrated to give a residue. 120 ml of toluene and 33 ml of 30% hydrogen peroxide solution were added dropwise to the residue and stirred by heating at 70 ° C. After heating at reflux for 1 h, the reaction mixture is allowed to come to room temperature, washed once with water, twice with 10% ferrous ammonium sulfate, and once with water. The toluene layer is dried over anhydrous magnesium sulfate and concentrated to give a crude product. The crude product is subjected to silica gel chromatography to give 26.2 g of 3-methyl-4-benzyloxy-5-methylphenol (93% yield).

0℃에서 교반하는, 6.3g의 3-에틸-4-벤질옥시-5-메틸페놀, 3.2g의 트리에틸아민 및 50ml의 클로로포름의 혼합물에, 4.0g의 벤조일 클로라이드를 적가한다. 실온에서 6시간 동안 교반한 후, 반응 혼합물을 감압 농축하여 잔류물을 수득한다. 잔류물에 100ml의 10% 염산을 첨가하고 이 혼합물을 100ml의 에틸 아세테이트로 추출한다. 에틸 아세테이트층을 10% 염산, 포화 탄산수소나트륨 수용액 및 포화 염수로 연속적으로 세척하고, 무수 황산 마그네슘으로 건조한 다음 감압 농축하여, 8.4g의 조 생성물 4-벤질옥시-3-에틸-5-메틸페닐 벤조에이트를 수득한다(수율 93%).4.0 g of benzoyl chloride is added dropwise to a mixture of 6.3 g of 3-ethyl-4-benzyloxy-5-methylphenol, 3.2 g of triethylamine and 50 ml of chloroform, stirred at 0 ° C. After stirring for 6 hours at room temperature, the reaction mixture is concentrated under reduced pressure to give a residue. To the residue is added 100 ml of 10% hydrochloric acid and the mixture is extracted with 100 ml of ethyl acetate. The ethyl acetate layer was washed successively with 10% hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 8.4 g of crude product 4-benzyloxy-3-ethyl-5-methylphenyl benzo. Obtained is yield (93% yield).

8.4g의 조 생성물 4-벤질옥시-3-에틸-5-메틸페닐 벤조에이트를 100ml의 에틸 아세테이트에 녹이고, 이것을 반응 용기에 충전시키고, 용기내의 공기를 질소기체로 대체한다. 0.5g의 10% 팔라듐/탄소를 첨가하고, 용기내의 질소 기체를 수소 기체로 대체한 다음, 실온에서 24시간 동안 격렬하게 교반한다. 용기내의 수소 기체를 질소 기체로 대체시키고 나서, 반응 혼합물을 세라이트(cerite)로 여과하고 여액을 농축하여, 5.9g의 조 생성물 3-에틸-4-히드록시-5-메틸페닐 벤조에이트를 수득한다(수율 95%).8.4 g of crude product 4-benzyloxy-3-ethyl-5-methylphenyl benzoate are dissolved in 100 ml of ethyl acetate, which is charged to a reaction vessel and the air in the vessel is replaced with a nitrogen gas. 0.5 g of 10% palladium / carbon is added and the nitrogen gas in the vessel is replaced with hydrogen gas and then vigorously stirred at room temperature for 24 hours. The hydrogen gas in the vessel is replaced with nitrogen gas, then the reaction mixture is filtered through cerite and the filtrate is concentrated to give 5.9 g of crude product 3-ethyl-4-hydroxy-5-methylphenyl benzoate. (Yield 95%).

0℃에서 교반하는, 0.87g의 3-에틸-5-메틸-4-(3-(4-트리플루오로메틸)벤즈아미도)프로필옥시페닐 벤조에이트 및 10ml의 메탄올의 혼합물에, 0.16g의 수산화 나트륨 및 2ml의 물의 혼합물을 첨가한다. 실온에서 24시간 동안 교반한 후, 반응 혼합물에 10% 염산을 첨가하여 약산성으로 만들고, 50ml의 에틸 아세테이트로 추출한다. 에틸 아세테이트층을 포화 염수로 세척하고 무수 황산마그네슘으로 건조한 다음 감압 농축하여 잔류물을 수득한다. 상기 잔류물을 실리카 겔 크로마토그래피하여, 0.66g의 3-에틸-5-메틸-4-(3-(4-트리플루오로메틸)벤즈아미도)프로필옥시페놀을 수득한다(수율 94%).0.16 g of a mixture of 0.87 g of 3-ethyl-5-methyl-4- (3- (4-trifluoromethyl) benzamido) propyloxyphenyl benzoate and 10 ml of methanol, stirred at 0 ° C A mixture of sodium hydroxide and 2 ml of water is added. After stirring for 24 h at room temperature, 10% hydrochloric acid is added to the reaction mixture to make it slightly acidic and extracted with 50 ml of ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a residue. The residue is subjected to silica gel chromatography to give 0.66 g of 3-ethyl-5-methyl-4- (3- (4-trifluoromethyl) benzamido) propyloxyphenol (yield 94%).

하기는 화학식 (4) 또는 (5)의 중간체의 일부 특정예를, 그의 화합물 번호 및 물리적 성질(측정될 경우)과 함께 기술하고 있다:The following describes some specific examples of the intermediates of formula (4) or (5), together with their compound number and physical properties (when measured):

82) 3,5-디클로로-4-(3-벤즈아미도프로필옥시)페놀82) 3,5-dichloro-4- (3-benzamidopropyloxy) phenol

83) 3,5-디클로로-4-(3-(4-클로로벤즈아미도프로필옥시)페놀83) 3,5-dichloro-4- (3- (4-chlorobenzamidopropyloxy) phenol

84) 3,5-디클로로-4-(3-(4-트리플루오로메틸벤즈아미도프로필옥시)페놀84) 3,5-dichloro-4- (3- (4-trifluoromethylbenzamidopropyloxy) phenol

85) 3,5-디클로로-4-(3-(4-트리플루오로메톡시벤즈아미도프로필옥시)페놀85) 3,5-dichloro-4- (3- (4-trifluoromethoxybenzamidopropyloxy) phenol

86) 3,5-디클로로-4-(4-벤즈아미도부틸옥시)페놀86) 3,5-dichloro-4- (4-benzamidobutyloxy) phenol

87) 3,5-디클로로-4-(4-(4-클로로벤즈아미도)부틸옥시)페놀87) 3,5-dichloro-4- (4- (4-chlorobenzamido) butyloxy) phenol

88) 3,5-디클로로-4-(4-(4-트리플루오로메틸벤즈아미도)부틸옥시)페놀88) 3,5-dichloro-4- (4- (4-trifluoromethylbenzamido) butyloxy) phenol

89) 3,5-디클로로-4-(4-(4-트리플루오로메톡시벤즈아미도)부틸옥시)페놀89) 3,5-dichloro-4- (4- (4-trifluoromethoxybenzamido) butyloxy) phenol

90) 3,5-디클로로-4-(3-(5-트리플루오로메틸피콜린아미도)프로필옥시)페놀90) 3,5-dichloro-4- (3- (5-trifluoromethylpicolinamido) propyloxy) phenol

91) 3,5-디클로로-4-(4-(5-트리플루오로메틸피콜린아미도)부틸옥시)페놀91) 3,5-dichloro-4- (4- (5-trifluoromethylpicolinamido) butyloxy) phenol

92) 3,5-디클로로-4-(3-(4-트리플루오로메틸벤젠술폰아미도)프로필옥시)페놀92) 3,5-dichloro-4- (3- (4-trifluoromethylbenzenesulfonamido) propyloxy) phenol

93) 3,5-디클로로-4-(4-(4-트리플루오로메틸벤젠술폰아미도)부틸옥시)페놀93) 3,5-dichloro-4- (4- (4-trifluoromethylbenzenesulfonamido) butyloxy) phenol

94) 3,5-디클로로-4-(3-(5-트리플루오로메틸피리딘-2-술폰아미도)프로폭시)페놀94) 3,5-dichloro-4- (3- (5-trifluoromethylpyridine-2-sulfonamido) propoxy) phenol

95) 3,5-디클로로-4-(4-(5-트리플루오로메틸피리딘-2-술폰아미도)부틸옥시)페놀95) 3,5-dichloro-4- (4- (5-trifluoromethylpyridine-2-sulfonamido) butyloxy) phenol

96) 3,5-디클로로-4-(3-(N-(4-트리플루오로메틸페닐)카르바모일)프로필옥시)페놀96) 3,5-dichloro-4- (3- (N- (4-trifluoromethylphenyl) carbamoyl) propyloxy) phenol

97) 3,5-디클로로-4-(4-(N-(4-트리플루오로메틸페닐)카르바모일)부틸옥시)페놀97) 3,5-dichloro-4- (4- (N- (4-trifluoromethylphenyl) carbamoyl) butyloxy) phenol

98) 3,5-디클로로-4-(3-(N-(4-트리플루오로메틸-2-피리딜)카르바모일)프로필옥시)페놀98) 3,5-dichloro-4- (3- (N- (4-trifluoromethyl-2-pyridyl) carbamoyl) propyloxy) phenol

99) 3,5-디클로로-4-(4-(N-(4-트리플루오로메틸-2-피리딜)카르바모일)부틸옥시)페놀99) 3,5-dichloro-4- (4- (N- (4-trifluoromethyl-2-pyridyl) carbamoyl) butyloxy) phenol

100) 3-클로로-5-메틸-4-(3-벤즈아미도프로필옥시)페놀100) 3-chloro-5-methyl-4- (3-benzamidopropyloxy) phenol

101) 3-클로로-5-메틸-4-(3-(4-클로로벤즈아미도프로필옥시)페놀101) 3-chloro-5-methyl-4- (3- (4-chlorobenzamidopropyloxy) phenol

102) 3-클로로-5-메틸-4-(3-(4-트리플루오로메틸벤즈아미도프로필옥시)페놀102) 3-chloro-5-methyl-4- (3- (4-trifluoromethylbenzamidopropyloxy) phenol

103) 3-클로로-5-메틸-4-(3-(4-트리플루오로메톡시벤즈아미도프로필옥시)페놀103) 3-chloro-5-methyl-4- (3- (4-trifluoromethoxybenzamidopropyloxy) phenol

104) 3-클로로-5-메틸-4-(4-벤즈아미도부틸옥시)페놀104) 3-chloro-5-methyl-4- (4-benzamidobutyloxy) phenol

105) 3-클로로-5-메틸-4-(4-(4-클로로벤즈아미도)부틸옥시)페놀105) 3-chloro-5-methyl-4- (4- (4-chlorobenzamido) butyloxy) phenol

106) 3-클로로-5-메틸-4-(4-(4-트리플루오로메틸벤즈아미도)부틸옥시)페놀106) 3-chloro-5-methyl-4- (4- (4-trifluoromethylbenzamido) butyloxy) phenol

107) 3-클로로-5-메틸-4-(4-(4-트리플루오로메톡시벤즈아미도)부틸옥시)페놀107) 3-chloro-5-methyl-4- (4- (4-trifluoromethoxybenzamido) butyloxy) phenol

108) 3-클로로-5-메틸-4-(3-(5-트리플루오로메틸피콜린아미도)프로필옥시)페놀.108) 3-chloro-5-methyl-4- (3- (5-trifluoromethylpicolinamido) propyloxy) phenol.

109) 3-클로로-5-메틸-4-(4-(5-트리플루오로메틸피콜린아미도)부틸옥시)페놀109) 3-chloro-5-methyl-4- (4- (5-trifluoromethylpicolinamido) butyloxy) phenol

110) 3-클로로-5-메틸-4-(3-(4-트리플루오로메틸벤젠술폰아미도)프로필옥시)페놀110) 3-chloro-5-methyl-4- (3- (4-trifluoromethylbenzenesulfonamido) propyloxy) phenol

111) 3-클로로-5-메틸-4-(4-(4-트리플루오로메틸벤젠술폰아미도)부틸옥시)페놀111) 3-chloro-5-methyl-4- (4- (4-trifluoromethylbenzenesulfonamido) butyloxy) phenol

112) 3-클로로-5-메틸-4-(3-(5-트리플루오로메틸피리딘-2-술폰아미도)프로필옥시)페놀112) 3-chloro-5-methyl-4- (3- (5-trifluoromethylpyridine-2-sulfonamido) propyloxy) phenol

113) 3-클로로-5-메틸-4-(4-(5-트리플루오로메틸피리딘-2-술폰아미도)부틸옥시)페놀113) 3-chloro-5-methyl-4- (4- (5-trifluoromethylpyridine-2-sulfonamido) butyloxy) phenol

114) 3,5-디클로로-4-(3-(N-(4-트리플루오로메틸페닐)카르바모일)프로필옥시)페놀114) 3,5-dichloro-4- (3- (N- (4-trifluoromethylphenyl) carbamoyl) propyloxy) phenol

115) 3-클로로-5-메틸-4-(4-(N-(4-트리플루오로메틸페닐)카르바모일)부틸옥시)페놀115) 3-chloro-5-methyl-4- (4- (N- (4-trifluoromethylphenyl) carbamoyl) butyloxy) phenol

116) 3-클로로-5-메틸-4-(3-(N-(5-트리플루오로메틸-2-피리딜)카르바모일)부틸옥시)페놀116) 3-chloro-5-methyl-4- (3- (N- (5-trifluoromethyl-2-pyridyl) carbamoyl) butyloxy) phenol

117) 3-클로로-5-메틸-4-(4-(N-(5-트리플루오로메틸-2-피리딜)카르바모일)부틸옥시)페놀117) 3-chloro-5-methyl-4- (4- (N- (5-trifluoromethyl-2-pyridyl) carbamoyl) butyloxy) phenol

118) 3-에틸-5-메틸-4-(3-벤즈아미도프로필옥시)페놀118) 3-ethyl-5-methyl-4- (3-benzamidopropyloxy) phenol

119) 3-에틸-5-메틸-4-(3-(4-클로로벤즈아미도프로필옥시)페놀119) 3-ethyl-5-methyl-4- (3- (4-chlorobenzamidopropyloxy) phenol

120) 3-에틸-5-메틸-4-(3-(4-트리플루오로메틸벤즈아미도프로필옥시)페놀120) 3-ethyl-5-methyl-4- (3- (4-trifluoromethylbenzamidopropyloxy) phenol

121) 3-에틸-5-메틸-4-(3-(4-트리플루오로메톡시벤즈아미도프로필옥시)페놀121) 3-ethyl-5-methyl-4- (3- (4-trifluoromethoxybenzamidopropyloxy) phenol

122) 3-에틸-5-메틸-4-(4-벤즈아미도부틸옥시)페놀122) 3-ethyl-5-methyl-4- (4-benzamidobutyloxy) phenol

123) 3-에틸-5-메틸-4-(4-(4-클로로벤즈아미도)부틸옥시)페놀123) 3-ethyl-5-methyl-4- (4- (4-chlorobenzamido) butyloxy) phenol

124) 3-에틸-5-메틸-4-(4-(4-트리플루오로메틸벤즈아미도)부틸옥시)페놀124) 3-ethyl-5-methyl-4- (4- (4-trifluoromethylbenzamido) butyloxy) phenol

125) 3-에틸-5-메틸-4-(4-(4-트리플루오로메톡시벤즈아미도)부틸옥시)페놀125) 3-ethyl-5-methyl-4- (4- (4-trifluoromethoxybenzamido) butyloxy) phenol

126) 3-에틸-5-메틸-4-(3-(5-트리플루오로메틸피콜린아미도)프로필옥시)페놀126) 3-ethyl-5-methyl-4- (3- (5-trifluoromethylpicolinamido) propyloxy) phenol

127) 3-에틸-5-메틸-4-(4-(5-트리플루오로메틸피콜린아미도)부틸옥시)페놀127) 3-ethyl-5-methyl-4- (4- (5-trifluoromethylpicolinamido) butyloxy) phenol

128) 3-에틸-5-메틸-4-(3-(4-트리플루오로메틸벤젠술폰아미도)프로필옥시)페놀128) 3-ethyl-5-methyl-4- (3- (4-trifluoromethylbenzenesulfonamido) propyloxy) phenol

129) 3-에틸-5-메틸-4-(4-(4-트리플루오로메틸벤젠술폰아미도)부틸옥시)페놀129) 3-ethyl-5-methyl-4- (4- (4-trifluoromethylbenzenesulfonamido) butyloxy) phenol

130) 3-에틸-5-메틸-4-(3-(5-트리플루오로메틸피리딘-2-술폰아미도)프로폭시)페놀130) 3-ethyl-5-methyl-4- (3- (5-trifluoromethylpyridine-2-sulfonamido) propoxy) phenol

131) 3-에틸-5-메틸-4-(4-(5-트리플루오로메틸피리딘-2-술폰아미도)부틸옥시)페놀131) 3-ethyl-5-methyl-4- (4- (5-trifluoromethylpyridine-2-sulfonamido) butyloxy) phenol

132) 3,5-디클로로-4-(3-(N-(4-트리플루오로메틸페닐)카르바모일)프로필옥시)페놀132) 3,5-dichloro-4- (3- (N- (4-trifluoromethylphenyl) carbamoyl) propyloxy) phenol

133) 3-에틸-5-메틸-4-(4-(N-(4-트리플루오로메틸페닐)카르바모일)부틸옥시)페놀133) 3-ethyl-5-methyl-4- (4- (N- (4-trifluoromethylphenyl) carbamoyl) butyloxy) phenol

134) 3-에틸-5-메틸-4-(3-(N-(5-트리플루오로메틸-2-피리딜)카르바모일)프로필옥시)페놀134) 3-ethyl-5-methyl-4- (3- (N- (5-trifluoromethyl-2-pyridyl) carbamoyl) propyloxy) phenol

135) 3-에틸-5-메틸-4-(4-(N-(5-트리플루오로메틸-2-피리딜)카르바모일)부틸옥시)페놀135) 3-ethyl-5-methyl-4- (4- (N- (5-trifluoromethyl-2-pyridyl) carbamoyl) butyloxy) phenol

136) 3,5-디클로로-4-(3-(2-푸란카르복사미도)프로필옥시)페놀136) 3,5-dichloro-4- (3- (2-furancarboxamido) propyloxy) phenol

137) 3,5-디클로로-4-(3-(2-푸란카르복사미도)부틸옥시)페놀137) 3,5-dichloro-4- (3- (2-furancarboxamido) butyloxy) phenol

138) 3,5-디클로로-4-(3-(3-푸란카르복사미도)프로필옥시)페놀138) 3,5-dichloro-4- (3- (3-furancarboxamido) propyloxy) phenol

139) 3,5-디클로로-4-(4-(3-푸란카르복사미도)부틸옥시)페놀139) 3,5-dichloro-4- (4- (3-furancarboxamido) butyloxy) phenol

140) 3,5-디클로로-4-(3-(5-브로모-2-푸란카르복사미도)프로필옥시)페놀140) 3,5-dichloro-4- (3- (5-bromo-2-furancarboxamido) propyloxy) phenol

141) 3,5-디클로로-4-(4-(5-브로모-2-푸란카르복사미도)부틸옥시)페놀141) 3,5-dichloro-4- (4- (5-bromo-2-furancarboxamido) butyloxy) phenol

142) 3,5-디클로로-4-(3-(2-티오펜카르복사미도)프로필옥시)페놀142) 3,5-dichloro-4- (3- (2-thiophenecarboxamido) propyloxy) phenol

143) 3,5-디클로로-4-(4-(2-티오펜카르복사미도)부틸옥시)페놀143) 3,5-dichloro-4- (4- (2-thiophenecarboxamido) butyloxy) phenol

144) 3,5-디클로로-4-(3-(3-티오펜카르복사미도)프로필옥시)페놀144) 3,5-dichloro-4- (3- (3-thiophenecarboxamido) propyloxy) phenol

145) 3,5-디클로로-4-(4-(3-티오펜카르복사미도)부틸옥시)페놀145) 3,5-dichloro-4- (4- (3-thiophenecarboxamido) butyloxy) phenol

146) 3,5-디클로로-4-(3-(5-메틸-2-티오펜카르복사미도)프로필옥시)페놀146) 3,5-dichloro-4- (3- (5-methyl-2-thiophenecarboxamido) propyloxy) phenol

147) 3,5-디클로로-4-(4-(5-메틸-2-티오펜카르복사미도)부틸옥시)페놀147) 3,5-dichloro-4- (4- (5-methyl-2-thiophenecarboxamido) butyloxy) phenol

148) 3,5-디클로로-4-(3-(2-피라진카르복사미도)프로필옥시)페놀148) 3,5-dichloro-4- (3- (2-pyrazinecarboxamido) propyloxy) phenol

149) 3,5-디클로로-4-(4-(2-피라진카르복사미도)부틸옥시)페놀149) 3,5-dichloro-4- (4- (2-pyrazinecarboxamido) butyloxy) phenol

150) 3,5-디클로로-4-(3-(1-메틸-2-인돌카르복사미도)프로필옥시)페놀150) 3,5-dichloro-4- (3- (1-methyl-2-indolecarboxamido) propyloxy) phenol

151) 3,5-디클로로-4-(4-(1-메틸-2-인돌카르복사미도)부틸옥시)페놀151) 3,5-dichloro-4- (4- (1-methyl-2-indolecarboxamido) butyloxy) phenol

152) 3,5-디클로로-4-(3-(1-메틸-2-피롤카르복사미도)프로필옥시)페놀152) 3,5-dichloro-4- (3- (1-methyl-2-pyrrolecarboxamido) propyloxy) phenol

153) 3,5-디클로로-4-(4-(1-메틸-2-피롤카르복사미도)부틸옥시)페놀153) 3,5-dichloro-4- (4- (1-methyl-2-pyrrolecarboxamido) butyloxy) phenol

154) 3,5-디클로로-4-(3-(2-퀴놀린카르복사미도)프로필옥시)페놀154) 3,5-dichloro-4- (3- (2-quinolinecarboxamido) propyloxy) phenol

155) 3,5-디클로로-4-(4-(2-퀴놀린카르복사미도)부틸옥시)페놀155) 3,5-dichloro-4- (4- (2-quinolinecarboxamido) butyloxy) phenol

156) 3,5-디클로로-4-(3-(5-메틸-2-피라진카르복사미도)프로필옥시)페놀156) 3,5-dichloro-4- (3- (5-methyl-2-pyrazinecarboxamido) propyloxy) phenol

157) 3,5-디클로로-4-(4-(5-메틸-2-피라진카르복사미도)부틸옥시)페놀.157) 3,5-dichloro-4- (4- (5-methyl-2-pyrazinecarboxamido) butyloxy) phenol.

하기의 제제예의 부는 중량부이며 본 발명에 의한 화합물은 상기 기술된 화합물 번호로 인식된다.Parts in the following formulation examples are parts by weight, and the compounds according to the present invention are recognized by the compound numbers described above.

제제예 1Formulation Example 1

유화성 농축물Emulsifiable concentrate

각각 10부의 본 발명에 의한 화합물 (1) 내지 (148)을, 35부의 크실렌 및 35부의 N,N-디메틸포르아미드에 녹이고, 여기에 14부의 폴리옥시에틸렌 스트릴페닐 에테르와 6부의 칼슘 도데실벤젠술포네이트를 첨가하고 이 혼합물을 잘 교반하여, 각 화합물의 10% 유화성 농축물을 수득한다.Each of 10 parts of the compound (1) to (148) according to the present invention was dissolved in 35 parts of xylene and 35 parts of N, N-dimethylformamide, where 14 parts of polyoxyethylene strylphenyl ether and 6 parts of calcium dodecyl were added. Benzenesulfonate is added and the mixture is stirred well to obtain a 10% emulsifiable concentrate of each compound.

제제예 2Formulation Example 2

습윤성 분말Wettable powder

각각 20부의 본 발명에 의한 화합물 (1) 내지 (148)을, 4부의 소듐 라우릴 술페이트, 2부의 칼슘 리그닌 술포네이트, 20부의 합성 이산화 규소 수화물 미분말 및 54부의 규조토의 혼합물에 첨가하고, 이 혼합물을 믹서로 교반하여, 각 화합물의 20% 유화성 농축물을 수득한다.20 parts each of compounds (1) to (148) according to the present invention are added to a mixture of 4 parts sodium lauryl sulfate, 2 parts calcium lignin sulfonate, 20 parts synthetic silicon dioxide hydrate fine powder and 54 parts diatomaceous earth, The mixture is stirred with a mixer to obtain a 20% emulsifiable concentrate of each compound.

제제예 3Formulation Example 3

과립Granules

각각 5부의 본 발명에 의한 화합물 (1) 내지 (148)을, 5부의 합성 이산화 규소 산화물 미분말, 5부의 소듐 도데실벤젠술포네이트, 30부의 벤토나이트 및 55부의 클레이를 혼합하고, 이 혼합물을 잘 교반한다. 그 다음 적절한 양의 물을 이 혼합물에 첨가하고, 추가로 교반하고 과립기로 과립화하고 나서 공기-건조시켜, 각 화합물의 5% 과립을 수득한다.To 5 parts of the compound (1) to (148) according to the present invention, 5 parts of synthetic silicon dioxide fine powder, 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite and 55 parts of clay are mixed, and the mixture is stirred well. do. Appropriate amount of water is then added to this mixture, further stirred, granulated with a granulator and then air-dried to give 5% granules of each compound.

제제예 4Formulation Example 4

분진Dust

각각 1부의 본 발명에 의한 화합물 (1) 내지 (148)을 적정량의 아세톤에 녹이고, 여기에 5부의 합성 이산화 규소 수화물 미분말, 0.3부의 PAP 및 93.7부의 클레이를 첨가하고, 이 혼합물을 믹서로 교반한다. 아세톤을 증발로 제거하여, 각 화합물의 1% 분진을 수득한다.Each of 1 part of the compounds (1) to (148) according to the present invention is dissolved in an appropriate amount of acetone, and 5 parts of synthetic silicon dioxide hydrate fine powder, 0.3 part of PAP and 93.7 parts of clay are added thereto, and the mixture is stirred with a mixer. . Acetone is removed by evaporation to give 1% dust of each compound.

제제예 5Formulation Example 5

유동성 물질Fluid material

각각 20부의 본 발명에 의한 화합물 (1) 내지 (148)을 1.5부의 소르비탄 트리올레에이트 및 2부의 폴리비닐 알코올을 함유하는 수용액 28.5부와 혼합하고, 이 혼합물을 샌드 그라인더로 입자 크기 3㎛의 미립자로 분쇄한 다음, 여기에 0.05부의 크산탐 검 및 0.1부의 알루미늄 마그네슘 실리케이트를 함유하고 있는 수용액 40부를 첨가하고 나서 10부의 프로필렌 글리콜을 첨가한다. 상기 혼합물을 교반하여, 각 화합물의 20% 물-기재 현탁물을 수득한다.20 parts each of the compounds (1) to (148) according to the present invention were mixed with 28.5 parts of an aqueous solution containing 1.5 parts of sorbitan trioleate and 2 parts of polyvinyl alcohol, and the mixture was mixed with a sand grinder having a particle size of 3 m. After grinding into fine particles, 40 parts of an aqueous solution containing 0.05 parts of xantham gum and 0.1 parts of aluminum magnesium silicate are added, followed by 10 parts of propylene glycol. The mixture is stirred to give 20% water-based suspension of each compound.

제제예 6Formulation Example 6

오일 분무물Oil spray

우선, 각각 20부의 본 발명에 의한 화합물 (1) 내지 (148)을 5부의 크실렌 및 5부의 트리클로로에탄에 녹인다. 그리고 나서, 이 용액을 89.9부의 탈취 케로신과 혼합하여, 각 화합물의 0.1% 오일 분무물을 수득한다.First, 20 parts of compounds (1) to (148) according to the present invention are dissolved in 5 parts of xylene and 5 parts of trichloroethane. This solution is then mixed with 89.9 parts of deodorized kerosine to obtain 0.1% oil spray of each compound.

제제예 7Formulation Example 7

오일-기재 에어로졸Oil-based aerosols

우선, 각각 0.1부의 본 발명에 의한 화합물 (1) 내지 (148)을, 0.2부의 테트라메트린, 0.1부의 d-페노트린 및 10부의 트리클로로에탄을 59.6부의 탈취 케로신에 녹이고, 이 용액을 에어로졸 용기에 충전시킨다. 그 다음 용기에 밸브를 장치하고, 이것을 통해 30부의 추진제(액화 석유 가스)를 증압하에 충전시켜, 각 화합물의 오일-기재 에어로졸을 수득한다.First, 0.1 parts of the compounds (1) to (148) according to the present invention were dissolved in 59.6 parts of deodorized kerosine in 0.2 parts of tetramethrin, 0.1 parts of d-phenotrine, and 10 parts of trichloroethane. Fill the aerosol container. The vessel is then equipped with a valve, through which 30 parts of propellant (liquefied petroleum gas) are charged under pressure to obtain an oil-based aerosol of each compound.

제제예 8Formulation Example 8

물-기재 에어로졸Water-based aerosol

에어로졸 용기를 각각 0.2부의 본 발명에 의한 화합물 (1) 내지 (148), 0.2부의 d-알레트린, 0.2부의 d-페노트린, 5부의 크실렌, 3.4부의 탈취 케로신 및 1부의 유화제[ATMOS 300(Atlas Chemical Co. 에서 상표명으로 등록함)]의 혼합물과 50부의 순수한 물로 충전시킨다. 그 다음 용기에 밸브를 장치하고, 이것을 통해 40부의 추진제(액화 석유 가스)를 증압하에 충전시켜, 각 화합물의 물-기재 에어로졸을 수득한다.The aerosol containers were respectively prepared with 0.2 parts of the compounds (1) to (148) according to the present invention, 0.2 parts of d-alletrin, 0.2 parts of d-phenotrine, 5 parts of xylene, 3.4 parts of deodorizing kerosine and 1 part of emulsifier [ATMOS 300 (Registered under the trade name of Atlas Chemical Co.)] and 50 parts of pure water. The vessel is then equipped with a valve, through which 40 parts of propellant (liquefied petroleum gas) are charged under pressure to obtain a water-based aerosol of each compound.

제제예 9Formulation Example 9

모기-코일Mosquito coil

우선, 각각 0.3g의 본 발명에 의한 화합물 (1) 내지 (148)을 0.3g의 d-알레트린과 혼합하고, 이 혼합물을 20ml의 아세톤에 녹인다. 교반하에 용액을 99.4g의 모기-코일용 운반체(타부 분말, 마크 분말 및 우드 반죽을 4:3:3의 비율로 혼합하여 제조)와 균일하게 혼합한다. 상기 혼합물을 120ml의 물로 잘 혼련하고 성형 및 건조시켜, 각 화합물의 모기-코일을 수득한다.First, 0.3 g of compounds (1) to (148) according to the present invention are mixed with 0.3 g of d-alletrin, respectively, and the mixture is dissolved in 20 ml of acetone. Under stirring, the solution is uniformly mixed with 99.4 g of mosquito-coil carrier (prepared by mixing tabu powder, mark powder and wood dough in a ratio of 4: 3: 3). The mixture is kneaded well with 120 ml of water, shaped and dried to give the mosquito-coil of each compound.

제제예 10Formulation Example 10

전자 모기-매트Electronic mosquito-mat

우선, 각각 0.4g의 본 발명에 의한 화합물 (1) 내지 (148), 0.4부의 d-알레트린 및 0.4g의 피페닐 부톡시드를 아세톤에 녹여 전체 부피를 10ml로 만든다. 그 다음, 0.5ml의 상기 용액을 크기가 2.5cm×1.5cm×0.3cm(목화 린트와 펄프의 가는 섬유화된 혼합물을 시트로 성형함으로써 제조)인 전자 모기-매트용 지지체에 균일하게 흡수시켜, 각 화합물의 전자 모기-매트를 수득한다.First, 0.4 g of the compounds (1) to (148) according to the present invention, 0.4 parts of d-alletrin and 0.4 g of fiphenyl butoxide are dissolved in acetone, respectively, to make a total volume of 10 ml. 0.5 ml of the solution was then uniformly absorbed into a support for an electronic mosquito-mat having a size of 2.5 cm x 1.5 cm x 0.3 cm (prepared by molding a thin fiberized mixture of cotton lint and pulp into sheets). Obtain an electronic mosquito-mat of the compound.

제제예 11Formulation Example 11

가열 훈연 제제Heated smoke preparations

우선, 각각 100㎎의 본 발명에 의한 화합물 (1) 내지 (148)을 적당량의 아세톤에 녹인다. 그 다음, 이 용액을 크기가 4.0cm×4.0cm×1.2cm인 다공성 세라믹 판에 흡수시켜, 각 화합물의 가열 훈연 제제를 수득한다.First, 100 mg of compounds (1) to (148) according to the present invention are dissolved in an appropriate amount of acetone, respectively. This solution is then absorbed into a porous ceramic plate having a size of 4.0 cm x 4.0 cm x 1.2 cm to obtain a heated smoking formulation of each compound.

제제예 12Formulation Example 12

독 미끼Poison bait

우선, 각각 100㎎의 본 발명에 의한 화합물 (1) 내지 (148)을 0.5ml의 아세톤에 녹이고, 이 용액을 5g의 동물용 고체 미끼 분말(사육용 고체 먹이 분말 CE-2, Japan Clea Co., Ltd.의 상표명)과 균일하게 혼합한다. 그 다음, 공기 건조에 의해 아세톤을 제거하여, 각 화합물의 0.5% 독 미끼를 수득한다.First, 100 mg of the compound (1) to (148) according to the present invention was dissolved in 0.5 ml of acetone, and the solution was dissolved in 5 g of animal solid bait powder (solid feed powder for breeding CE-2, Japan Clea Co. And brand names of the company. Acetone is then removed by air drying to yield 0.5% poison bait of each compound.

하기의 시험예는 본 발명에 의한 화합물이 살충제의 활성 성분으로서 유용함을 증명한다. 상기 시험예에서 본 발명에 의한 화합물은 상기에 기술된 화합물 번호로 구별되며, 비교를 위해 사용된 화합물은 표 35에 보여진 화합물 기호로 구별된다.The following test examples demonstrate that the compounds according to the invention are useful as active ingredients of pesticides. In the above test examples, the compounds according to the present invention are distinguished by the compound numbers described above, and the compounds used for the comparison are distinguished by the compound symbols shown in Table 35.

[표 35]Table 35

시험예 1Test Example 1

스포돕테라 리투라(Spodoptera litura)에 대한 살충 시험Insecticidal test for Spodoptera litura

직경이 11cm인 폴리에틸렌 컵에서, 제제예 1에서 수득한 시험 화합물의 유화성 농축물의 200배의 물 희석물(500ppm)을, 스포돕테라 리투라용 인공 먹이 13g에 2ml의 부피로 흡수시킨다. 스포돕테라 리투라의 네 번째-인스타(instar) 유충 10마리를 컵에서 발견하였다. 6일 후, 유충은 죽은 것으로 조사되었다. 시험은 2회 반복 실시하였다.In a polyethylene cup with a diameter of 11 cm, a 200-fold water dilution (500 ppm) of the emulsifiable concentrate of the test compound obtained in Formulation Example 1 is absorbed in a volume of 2 ml in 13 g of artificial feed for Spodhodera litura. Ten fourth-instar larvae of the Spodogerra litura were found in the cups. After 6 days, the larvae were found dead. The test was repeated twice.

결과로서, 본 발명에 의한 화합물 (1)-(7), (9), (11)-(21), (23)-(25), (27)-(30), (32)-(34), (44), (56), (58), (59), (67), (84), (86), (89)-(104), (108), (110), (111), (114)-(118), (120), (121), (124)-(127) 및 (129)-(133)은 80% 이상의 치사율을 나타낸다는 것을 발견하였다. 반대로, 비교용의 화합물 (A)와 (B)는 모두 0%의 치사율을 나타내었다.As a result, the compounds (1)-(7), (9), (11)-(21), (23)-(25), (27)-(30), (32)-(34 according to the present invention ), (44), (56), (58), (59), (67), (84), (86), (89)-(104), (108), (110), (111), (114)-(118), (120), (121), (124)-(127) and (129)-(133) were found to exhibit mortality of at least 80%. In contrast, both the compounds (A) and (B) for comparison showed 0% mortality.

시험예 2Test Example 2

플루텔라 크실로스델라(Plutella xylostella)에 대한 살충 시험Insecticidal test for Flutella xylostella

제제예 1에서 수득한 시험 화합물의 유화성 농축물의 물 희석물(25ppm)을, 병에 넣은 다섯 잎 단계의 양배추 위로 충분한 부피로 분무한다. 공기 건조한 후, 플루텔라 크실로스텔라의 세 번째-인스타(instar) 유충 10마리를 컵에서 발견하였다. 4일 후, 유충은 죽은 것으로 조사되었다.A water dilution (25 ppm) of the emulsifiable concentrate of the test compound obtained in Formulation Example 1 is sprayed in a sufficient volume over the bottled five leaf cabbage. After air drying, ten third-instar larvae of flutella xylostella were found in the cup. After 4 days, the larvae were found dead.

결과로서, 본 발명에 의한 화합물 (1), (2), (4), (6), (7), (12)-(14), (18)-(21), (33), (34), (44), (58), (59), (67), (84), (86), (89), (90), (97), (98) 및 (108)은 80% 이상의 치사율을 나타낸다는 것을 발견하였다. 반대로, 비교용의 화합물 (A)와 (B)는 모두 0%의 치사율을 나타내었다.As a result, the compounds (1), (2), (4), (6), (7), (12)-(14), (18)-(21), (33), and (34) according to the present invention. ), (44), (58), (59), (67), (84), (86), (89), (90), (97), (98), and (108) have a mortality of 80% or more. Was found. In contrast, both the compounds (A) and (B) for comparison showed 0% mortality.

시험예 3Test Example 3

크나팔로크로시스 메디날리스(Cnaphalocrocis medinalis)에 대한 살충 시험Insecticidal test for Cnaphalocrocis medinalis

제제예 1에서 수득한 시험 화합물의 유화성 농축물의 물 희석물(25ppm)을, 찻종 모양의 파종벼(Nihonbare)의 잎 위로 충분한 부피로 분무한다. 화학용액을 공기 건조한 후, 크나팔로크로시스 메디날리스 세 번째-인스타(instar) 유충 10마리를 컵에서 발견하였다. 4일 후, 유충은 죽은 것으로 조사되었다.A water dilution (25 ppm) of the emulsifiable concentrate of the test compound obtained in Formulation Example 1 is sprayed in a sufficient volume onto the leaves of tea seed-shaped soybean (Nihonbare). After the chemical solution was air dried, ten Knapallocsis Medialis third-instar larvae were found in the cups. After 4 days, the larvae were found dead.

결과로서, 본 발명에 의한 화합물 (1), (2), (4)-(7), (13), (14), (17), (18), (21), (32), (34), (56), (58), (59), (67), (89), (93) 및 (127)은 80% 이상의 치사율을 나타낸다는 것을 발견하였다. 반대로, 비교용의 화합물 (A)와 (B)는 모두 0%의 치사율을 나타내었다.As a result, the compounds (1), (2), (4)-(7), (13), (14), (17), (18), (21), (32), and (34) according to the present invention. ), (56), (58), (59), (67), (89), (93) and (127) were found to exhibit a mortality of at least 80%. In contrast, both the compounds (A) and (B) for comparison showed 0% mortality.

본 발명에 의한 화합물은 뛰어난 살충 활성을 가지고 있어서 해충의 억제를 위해 만족스러울만큼 효과적이다.The compounds according to the invention have excellent pesticidal activity and are satisfactorily effective for the control of pests.

Claims (80)

하기 화학식 (1)의 디할로프로펜 화합물:Dihalopropene compound of formula (1) [화학식 1][Formula 1] [식 중, m은 0 내지 4의 정수이고;[Wherein m is an integer of 0 to 4; n은 0 내지 2의 정수이며;n is an integer from 0 to 2; X는 독립적으로 염소 또는 브롬이고;X is independently chlorine or bromine; Y는 산소, NH 또는 황이며;Y is oxygen, NH or sulfur; Z는 산소, 황 또는 NR15(식 중, R15는 수소 또는 C1-C3알킬이다)이고;Z is oxygen, sulfur or NR 15 , wherein R 15 is hydrogen or C 1 -C 3 alkyl; R2, R3및 R4는 독립적으로 할로겐, C1-C3할로알킬 또는 C1-C3알킬이며;R 2 , R 3 and R 4 are independently halogen, C 1 -C 3 haloalkyl or C 1 -C 3 alkyl; R5, R6및 R7는 독립적으로 수소, C1-C3알킬 또는 트리플루오로메틸이고;R 5 , R 6 and R 7 are independently hydrogen, C 1 -C 3 alkyl or trifluoromethyl; L은 C=W, C(=W)NR13, NR13C(=W), SO2NR13, NR13SO2, NR13C(=W1)W, WC(=W1)NR13또는 NR14C(=W)NR13(식 중, W 및 W1은 독립적으로 산소 또는 황이고, R13및 R14는 독립적으로 수소, C1-C10알킬, C1-C5할로알킬, C2-C10알케닐, C2-C6할로알케닐, C3-C9알키닐 또는 C3-C5할로알키닐이다)이고;L is C = W, C (= W) NR 13 , NR 13 C (= W), SO 2 NR 13 , NR 13 SO 2 , NR 13 C (= W 1 ) W, WC (= W 1 ) NR 13 Or NR 14 C (═W) NR 13 wherein W and W 1 are independently oxygen or sulfur, and R 13 and R 14 are independently hydrogen, C 1 -C 10 alkyl, C 1 -C 5 haloalkyl , C 2 -C 10 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 9 alkynyl or C 3 -C 5 haloalkynyl); R1은 C1-C10알킬, C1-C5할로알킬, C2-C10알케닐, C2-C6할로알케닐, C3-C9알키닐, C3-C5할로알키닐, C2-C7알콕시알킬, C2-C7알킬티오알킬,R 1 is C 1 -C 10 alkyl, C 1 -C 5 haloalkyl, C 2 -C 10 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 9 alkynyl, C 3 -C 5 haloalky Nyl, C 2 -C 7 alkoxyalkyl, C 2 -C 7 alkylthioalkyl, C1-C4알킬, C1-C4알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 C3-C6시클로알킬,C 3 -C 6 cycloalkyl, which may be substituted with C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 1 -C 3 haloalkoxy, C1-C4알킬로 치환될 수도 있는 C4-C9시클로알킬알킬,C 4 -C 9 cycloalkylalkyl, which may be substituted with C 1 -C 4 alkyl, C1-C4알킬로 치환될 수도 있는 C5-C6시클로알케닐,C 5 -C 6 cycloalkenyl, which may be substituted with C 1 -C 4 alkyl, C1-C4알킬로 치환될 수도 있는 C6-C8시클로알케닐알킬,C 6 -C 8 cycloalkenylalkyl, which may be substituted with C 1 -C 4 alkyl, 또는 하기 화학식 Q1, Q2, Q3또는 Q4의, 치환될 수도 있는 복소환 기이다:Or a heterocyclic group which may be substituted, of the formula Q 1 , Q 2 , Q 3 or Q 4 : [식 중, M은 산소, NH 또는 황이고,[Wherein M is oxygen, NH or sulfur, l은 0 내지 5의 정수이고,l is an integer from 0 to 5, p는 0 내지 5의 정수이고,p is an integer from 0 to 5, q는 1 내지 5의 정수이며;q is an integer from 1 to 5; R12는 할로겐, 시아노, 니트로, 펜타플루오로술파닐(F5S). C1-C8알킬, C1-C3할로알킬, C1-C7알콕시, C1-C3할로알콕시, C1-C3알킬티오, C1-C3할로알칼티오, C3-C6알케닐옥시, C3-C6할로알케닐옥시, C1-C3히드록시알킬, C2-C4알케닐, C2-C4할로알케닐, C2-C4알키닐, C2-C4알키닐옥시, C2-C4할로알키닐, C2-C4할로알키닐옥시, C2-C4알콕시알킬, C2-C4알킬티오알킬, C3-C6시클로알킬, C5-C6시클로알케닐, C2-C5알콕시카르보닐, C3-C6시클로알킬옥시, C5-C6시클로알케닐옥시,R 12 is halogen, cyano, nitro, pentafluorosulfanyl (F 5 S). C 1 -C 8 alkyl, C 1 -C 3 haloalkyl, C 1 -C 7 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkalthio, C 3- C 6 alkenyloxy, C 3 -C 6 haloalkenyloxy, C 1 -C 3 hydroxyalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 alkynyloxy, C 2 -C 4 haloalkynyl, C 2 -C 4 haloalkynyloxy, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkylthioalkyl, C 3 -C 6 Cycloalkyl, C 5 -C 6 cycloalkenyl, C 2 -C 5 alkoxycarbonyl, C 3 -C 6 cycloalkyloxy, C 5 -C 6 cycloalkenyloxy, 할로겐, C1-C4알킬, C1-C3할로알킬, C1-C3알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 페닐,Phenyl which may be substituted by halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy, 할로겐, C1-C4알킬, C1-C3할로알킬, C1-C3알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 페녹시,Phenoxy, which may be substituted by halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy, 할로겐, C1-C4알킬, C1-C3할로알킬, C1-C3알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 벤질,Benzyl, which may be substituted by halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy, 할로겐, C1-C4알킬, C1-C3할로알킬, C1-C3알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 벤질옥시이거나;Benzyloxy which may be substituted by halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy; 또는 l이 2 내지 5의 정수일 때, 인접한 두 R12는 그들의 말단부에서 함께 결합하여 트리메틸렌이나 테트라메틸렌, 할로겐이나 C1-C3알킬로 치환될 수도 있는 메틸렌디옥시, 또는 할로겐이나 C1-C3알킬로 치환될 수도 있는 에틸렌디옥시를 형성하며; 그리고Or when l is an integer from 2 to 5, two adjacent R 12 's are bonded together at their termini to methylenedioxy, which may be substituted with trimethylene or tetramethylene, halogen or C 1 -C 3 alkyl, or halogen or C 1- Forms ethylenedioxy, which may be substituted with C 3 alkyl; And R8, R9, R10및 R11은 독립적으로 수소, C1-C3알킬 또는 트리플루오로메틸이다].R 8 , R 9 , R 10 and R 11 are independently hydrogen, C 1 -C 3 alkyl or trifluoromethyl. 제1항에 있어서, R13및 R14가 독립적으로 수소 또는 C1-C3알킬인 것을 특징으로 하는 디할로프로펜 화합물.The dihalopropene compound of claim 1, wherein R 13 and R 14 are independently hydrogen or C 1 -C 3 alkyl. 제1항 또는 제2항에 있어서, R1이 C1-C10알킬, C1-C5할로알킬, C2-C10알케닐, C2-C6할로알케닐, C3-C9알키닐 또는 C3-C5할로알키닐인 것을 특징으로 하는 디할로프로펜 화합물.3. The compound of claim 1, wherein R 1 is C 1 -C 10 alkyl, C 1 -C 5 haloalkyl, C 2 -C 10 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 9 Dihalopropene compound, which is alkynyl or C 3 -C 5 haloalkynyl. 제1항 내지 제3항 중의 어느 한 항에 있어서, L이 C(=W)NR13인 것을 특징으로 하는 디할로프로펜 화합물.The dihalopropene compound according to any one of claims 1 to 3, wherein L is C (= W) NR 13 . 제1항 또는 제2항에 있어서, R1이 Q1, Q2, Q3또는 Q4인 것을 특징으로 하는 디할로프로펜 화합물.The dihalopropene compound according to claim 1 or 2, wherein R 1 is Q 1 , Q 2 , Q 3 or Q 4 . 제1항 또는 제2항에 있어서, R1이 Q1인 것을 특징으로 하는 디할로프로펜 화합물.The dihalopropene compound according to claim 1 or 2, wherein R 1 is Q 1 . 제1항 또는 제2항에 있어서, R1이 Q1이고, L은 C=W, C(=W)NR13또는 SO2NR13인 것을 특징으로 하는 디할로프로펜 화합물.3. The dihalopropene compound according to claim 1, wherein R 1 is Q 1 and L is C═W, C (═W) NR 13 or SO 2 NR 13 . 제1항 또는 제2항에 있어서, R1이 Q1이고, L은 C(=W)NR13또는 SO2NR13인 것을 특징으로 하는 디할로프로펜 화합물.The dihalopropene compound according to claim 1 or 2, wherein R 1 is Q 1 and L is C (= W) NR 13 or SO 2 NR 13 . 제1항 또는 제2항에 있어서, R1이 Q1이고, L은 C(=W)NR13인 것을 특징으로 하는 디할로프로펜 화합물.The dihalopropene compound according to claim 1 or 2, wherein R 1 is Q 1 and L is C (= W) NR 13 . 제1항 또는 제2항에 있어서, R1은 p=0인 Q1이고, L은 C=W, C(=W)NR13또는 SO2NR13인 것을 특징으로 하는 디할로프로펜 화합물.3. The dihalopropene compound according to claim 1, wherein R 1 is Q 1 with p = 0 and L is C═W, C (═W) NR 13 or SO 2 NR 13. 4 . 제1항 또는 제2항에 있어서, R1은 p=0인 Q1이고, L은 C(=W)NR13또는 SO2NR13인 것을 특징으로 하는 디할로프로펜 화합물.3. The dihalopropene compound according to claim 1, wherein R 1 is Q 1 with p = 0 and L is C (═W) NR 13 or SO 2 NR 13. 4 . 제1항 또는 제2항에 있어서, R1은 p=0인 Q1이고, L은 C(=W)NR13인 것을 특징으로 하는 디할로프로펜 화합물.3. The dihalopropene compound according to claim 1, wherein R 1 is Q 1 with p = 0 and L is C (═W) NR 13. 4 . 제1항 또는 제2항에 있어서, R1이,The compound of claim 1 or 2, wherein R 1 is 1종 이상의 산소, 황 또는 질소 원자를 함유하고 있으며 (R16)S[식 중, R16은 할로겐, 니트로, 시아노, C1-C4알킬, C1-C3할로알킬, C1-C4알콕시, C1-C3할로알콕시, C1-C3알킬티오, C1-C3할로알킬티오, C1-C2알킬술피닐, C1-C2알킬술포닐, C1-C2할로알킬술포닐, C1-C2할로알킬술포닐, C2-C4알케닐, C2-C4할로알케닐, C2-C4알키닐, C2-C4할로알키닐, 아미노, 디메틸아미노, 아세트아미도, 아세틸, 할로아세틸, 포르밀, 카르복실, 메톡시카르보닐, C3-C6시클로알킬, (C1-C2알킬)아미노카르보닐, [디(C1-C2알킬)아미노]카르보닐,Containing one or more oxygen, sulfur, or nitrogen atoms (R 16 ) S [wherein R 16 represents halogen, nitro, cyano, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1- C 4 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, C 1 -C 2 alkylsulfinyl, C 1 -C 2 alkylsulfonyl, C 1- C 2 haloalkylsulfonyl, C 1 -C 2 haloalkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl , Amino, dimethylamino, acetamido, acetyl, haloacetyl, formyl, carboxyl, methoxycarbonyl, C 3 -C 6 cycloalkyl, (C 1 -C 2 alkyl) aminocarbonyl, [di (C 1 -C 2 alkyl) amino] carbonyl, 할로겐, C1-C4알킬, C1-C3할로알킬, C1-C4알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 페닐,Phenyl which may be substituted by halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 3 haloalkoxy, 할로겐, C1-C4알킬, C1-C3할로알킬, C1-C4알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 벤질,Benzyl, which may be substituted by halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 3 haloalkoxy, 할로겐, C1-C4알킬, C1-C3할로알킬, C1-C4알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 페녹시,Phenoxy, which may be substituted by halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 3 haloalkoxy, 할로겐, C1-C4알킬, C1-C3할로알킬, C1-C4알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 벤질옥시,Benzyloxy, which may be substituted by halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 3 haloalkoxy, 또는 할로겐, C1-C4알킬, C1-C3할로알킬, C1-C4알콕시 또는 C1-C3할로알콕시로 치환될 수도 있는 피리딜옥시이고; s는 0 내지 7의 정수이다]으로 치환될 수도 있는 5- 또는 6-원 복소환 기인 것을 특징으로 하는 디할로프로펜 화합물.Or pyridyloxy which may be substituted by halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 3 haloalkoxy; s is an integer of 0 to 7]. A dihalopropene compound, characterized in that it is a 5- or 6-membered heterocyclic group which may be substituted. 제13항에 있어서, 5- 또는 6-원 복소환 기가 2-피라지닐, 2-인돌릴, 2-피롤릴, 2-퀴놀릴, 2-티에닐, 3-티에닐, 2-푸릴, 3-푸릴, 2-피리딜, 3-피리딜 또는 4-피리딜인 것을 특징으로 하는 디할로프로펜 화합물.The compound of claim 13, wherein the 5- or 6-membered heterocyclic group is 2-pyrazinyl, 2-indolyl, 2-pyrrolyl, 2-quinolyl, 2-thienyl, 3-thienyl, 2-furyl, 3 -Dihalopropene compound, characterized in that it is furyl, 2-pyridyl, 3-pyridyl or 4-pyridyl. 제13항에 있어서, 5- 또는 6-원 복소환 기가 2-피라지닐, 2-인돌릴, 2-피롤릴, 2-퀴놀릴, 2-티에닐, 3-티에닐, 2-푸릴, 3-푸릴, 2-피리딜, 3-피리딜 또는 4-피리딜이고, L이 C=W, C(=W)NR13또는 SO2NR13인 것을 특징으로 하는 디할로프로펜 화합물.The compound of claim 13, wherein the 5- or 6-membered heterocyclic group is 2-pyrazinyl, 2-indolyl, 2-pyrrolyl, 2-quinolyl, 2-thienyl, 3-thienyl, 2-furyl, 3 -Furyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, wherein L is C = W, C (= W) NR 13 or SO 2 NR 13 . 제13항에 있어서, 5- 또는 6-원 복소환 기가 2-피라지닐, 2-인돌릴, 2-피롤릴, 2-퀴놀릴, 2-티에닐, 3-티에닐, 2-푸릴, 3-푸릴, 2-피리딜, 3-피리딜 또는 4-피리딜이고, L이 C(=W)NR13또는 SO2NR13인 것을 특징으로 하는 디할로프로펜 화합물.The compound of claim 13, wherein the 5- or 6-membered heterocyclic group is 2-pyrazinyl, 2-indolyl, 2-pyrrolyl, 2-quinolyl, 2-thienyl, 3-thienyl, 2-furyl, 3 -Furyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, wherein L is C (= W) NR 13 or SO 2 NR 13 . 제13항에 있어서, 5- 또는 6-원 복소환 기가 2-피라지닐, 2-인돌릴, 2-피롤릴, 2-퀴놀릴, 2-티에닐, 3-티에닐, 2-푸릴, 3-푸릴, 2-피리딜, 3-피리딜 또는 4-피리딜이고, L이 C(=W)NR13인 것을 특징으로 하는 디할로프로펜 화합물.The compound of claim 13, wherein the 5- or 6-membered heterocyclic group is 2-pyrazinyl, 2-indolyl, 2-pyrrolyl, 2-quinolyl, 2-thienyl, 3-thienyl, 2-furyl, 3 Dihalopropene compound wherein furyl, 2-pyridyl, 3-pyridyl or 4-pyridyl and L is C (= W) NR 13 . 제13항에 있어서, 5- 또는 6-원 복소환 기가 1-피롤리디닐 또는 1-피페리딜이고, L이 C=W 또는 C(=W)NR13인 것을 특징으로 하는 디할로프로펜 화합물.The dihalopropene according to claim 13, wherein the 5- or 6-membered heterocyclic group is 1-pyrrolidinyl or 1-piperidyl and L is C = W or C (= W) NR 13 . compound. 제1항 또는 제2항에 있어서, R2및 R3및 R4가 독립적으로 할로겐 또는 C1-C3알킬인 것을 특징으로 하는 디할로프로펜 화합물.The dihalopropene compound according to claim 1 or 2, wherein R 2 and R 3 and R 4 are independently halogen or C 1 -C 3 alkyl. 제1항 또는 제2항에 있어서, R2와 R3가 모두 염소이고, R4는 수소인 것을 특징으로 하는 디할로프로펜 화합물.The dihalopropene compound according to claim 1 or 2, wherein both R 2 and R 3 are chlorine and R 4 is hydrogen. 제1항 또는 제2항에 있어서, Y와 Z가 모두 산소인 것을 특징으로 하는 디할로프로펜 화합물.The dihalopropene compound according to claim 1 or 2, wherein both Y and Z are oxygen. 제1항 또는 제2항에 있어서, R5, R6및 R7이 독립적으로 수소 또는 C1-C3알킬인 것을 특징으로 하는 디할로프로펜 화합물.The dihalopropene compound according to claim 1 or 2, wherein R 5 , R 6 and R 7 are independently hydrogen or C 1 -C 3 alkyl. 제1항 또는 제2항에 있어서, R5, R6및 R7이 모두 수소인 것을 특징으로 하는 디할로프로펜 화합물.The dihalopropene compound according to claim 1 or 2, wherein R 5 , R 6 and R 7 are all hydrogen. 제1항 내지 제3항 중의 어느 한 항에 있어서, L이 WC(=W1)NR13인 것을 특징으로 하는 디할로프로펜 화합물.The dihalopropene compound according to any one of claims 1 to 3, wherein L is WC (= W 1 ) NR 13 . 제1항 내지 제24항 중의 어느 한 항에 기술된 디할로프로펜 화합물을 활성 성분으로서 함유하고 있는 살충제.A pesticide containing the dihalopropene compound according to any one of claims 1 to 24 as an active ingredient. 하기 화학식 (3)의 화합물:A compound of formula (3) [화학식 3][Formula 3] [식 중, X는 독립적으로 염소 또는 브롬이고;[Wherein X is independently chlorine or bromine; R18및 R19는 독립적으로 할로겐 또는 C1-C3알킬이며;R 18 and R 19 are independently halogen or C 1 -C 3 alkyl; R17은 아미노 또는 카르복실이고;R 17 is amino or carboxyl; R5, R6및 R7은 독립적으로 수소, C1-C3알킬 또는 트리플루오로메틸이며;R 5 , R 6 and R 7 are independently hydrogen, C 1 -C 3 alkyl or trifluoromethyl; m은 0 내지 4의 정수이다].m is an integer from 0 to 4; 제26항에 있어서, R5, R6및 R7이 모두 수소이고, m이 2 또는 3의 정수인 것을 특징으로 하는 화합물.27. The compound of claim 26, wherein R 5 , R 6 and R 7 are all hydrogen and m is an integer of 2 or 3. 3,5-디클로로-4-(3-아미노프로필옥시)-1-(3,3-디클로로-2-프로페닐옥시)-벤젠.3,5-dichloro-4- (3-aminopropyloxy) -1- (3,3-dichloro-2-propenyloxy) -benzene. 3,5-디클로로-4-(3-아미노프로필옥시)-1-(3,3-디브로모-2-프로페닐옥시)-벤젠.3,5-dichloro-4- (3-aminopropyloxy) -1- (3,3-dibromo-2-propenyloxy) -benzene. 3,5-디클로로-4-(3-아미노부틸옥시)-1-(3,3-디클로로-2-프로페닐옥시)-벤젠.3,5-dichloro-4- (3-aminobutyloxy) -1- (3,3-dichloro-2-propenyloxy) -benzene. 3,5-디클로로-4-(4-아미노부틸옥시)-1-(3,3-디브로모-2-프로페닐옥시)-벤젠.3,5-dichloro-4- (4-aminobutyloxy) -1- (3,3-dibromo-2-propenyloxy) -benzene. 4-(2,6-디클로로-4-(3,3-디클로로-2-프로페닐옥시)페녹시)부티르산.4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyric acid. 4-(2,6-디클로로-4-(3,3-디브로모-2-프로페닐옥시)페녹시)부티르산.4- (2,6-dichloro-4- (3,3-dibromo-2-propenyloxy) phenoxy) butyric acid. 5-(2,6-디클로로-4-(3,3-디클로로-2-프로페닐옥시)페녹시)발레르산.5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) valeric acid. 5-(2,6-디클로로-4-(3,3-디브로모-2-프로페닐옥시)페녹시)발레르산.5- (2,6-dichloro-4- (3,3-dibromo-2-propenyloxy) phenoxy) valeric acid. 하기 화학식 (4)의 페놀 화합물:Phenolic Compounds of Formula (4) [화학식 4][Formula 4] [식 중, R20은 제1항에서 정의된 Q1이거나, 제13항에서 정의된 R1(식 중, 5- 또는 6-원 복소환 기는 2-피라지닐, 2-인돌릴, 2-피롤릴, 2-퀴놀릴, 2-티에닐, 3-티에닐, 2-푸릴, 3-푸릴, 2-피리딜, 3-피리딜 또는 4-피리딜이다)이며;[Wherein R 20 is Q 1 as defined in claim 1 or R 1 as defined in claim 13 (wherein a 5- or 6-membered heterocyclic group is 2-pyrazinyl, 2-indolyl, 2- Pyrrolyl, 2-quinolyl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-pyridyl, 3-pyridyl or 4-pyridyl); R2및 R3는 독립적으로 할로겐, C1-C3할로알킬 또는 C1-C3알킬이고;R 2 and R 3 are independently halogen, C 1 -C 3 haloalkyl or C 1 -C 3 alkyl; R5, R6및 R7은 독립적으로 수소, C1-C3알킬 또는 트리플루오로메틸이며;R 5 , R 6 and R 7 are independently hydrogen, C 1 -C 3 alkyl or trifluoromethyl; L1은 C=W, C(=W)NR13또는 SO2NR13(식 중, W는 산소 또는 황이고, R131은 수소 또는 C1-C3알킬이다)이고;L 1 is C = W, C (= W) NR 13 or SO 2 NR 13 , wherein W is oxygen or sulfur and R 131 is hydrogen or C 1 -C 3 alkyl; m은 0 내지 4의 정수이다].m is an integer from 0 to 4; 제36항에 있어서, 5- 또는 6-원 복소환 기가 2-피리딜, 3-피리딜 또는 4-피리딜인 것을 특징으로 하는 페놀 화합물.37. The phenolic compound of claim 36, wherein the 5- or 6-membered heterocyclic group is 2-pyridyl, 3-pyridyl or 4-pyridyl. 제36항 또는 제37항에 있어서, R20은 p=0인 Q1이거나, 제13항에서 정의된 R1(식 중, 5- 또는 6-원 복소환 기가 2-피라지닐, 2-인돌릴, 2-피롤릴, 2-퀴놀릴, 2-티에닐, 3-티에닐, 2-푸릴, 3-푸릴, 2-피리딜, 3-피리딜 또는 4-피리딜이다)인 것을 특징으로 하는 페놀 화합물.38. The compound of claim 36 or 37, wherein R 20 is Q 1 with p = 0, or R 1 as defined in claim 13 wherein the 5- or 6-membered heterocyclic group is 2-pyrazinyl, 2-indole. Reel, 2-pyrrolyl, 2-quinolyl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-pyridyl, 3-pyridyl or 4-pyridyl) Phenolic compound. 제36항 또는 제37항에 있어서, R20은 p=0인 Q1이거나, 제13항에서 정의된 R1(식 중, 5- 또는 6-원 복소환 기가 2-피라지닐, 2-인돌릴, 2-피롤릴, 2-퀴놀릴, 2-티에닐, 3-티에닐, 2-푸릴, 3-푸릴, 2-피리딜, 3-피리딜 또는 4-피리딜이다)이며;38. The compound of claim 36 or 37, wherein R 20 is Q 1 with p = 0, or R 1 as defined in claim 13 wherein the 5- or 6-membered heterocyclic group is 2-pyrazinyl, 2-indole. Aryl, 2-pyrrolyl, 2-quinolyl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-pyridyl, 3-pyridyl or 4-pyridyl); L1은 C(=W)NR13또는 SO2NR131인 것을 특징으로 하는 페놀 화합물.L 1 is C (= W) NR 13 or SO 2 NR 131 . 제36항 또는 제37항에 있어서, R20은 p=0인 Q1이거나, 제13항에서 정의된 R1(식 중, 5- 또는 6-원 복소환 기가 2-피라지닐, 2-인돌릴, 2-피롤릴, 2-퀴놀릴, 2-티에닐, 3-티에닐, 2-푸릴, 3-푸릴, 2-피리딜, 3-피리딜 또는 4-피리딜이다)이며;38. The compound of claim 36 or 37, wherein R 20 is Q 1 with p = 0, or R 1 as defined in claim 13 wherein the 5- or 6-membered heterocyclic group is 2-pyrazinyl, 2-indole. Aryl, 2-pyrrolyl, 2-quinolyl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-pyridyl, 3-pyridyl or 4-pyridyl); R2및 R3는 할로겐 또는 C1-C3알킬이고;R 2 and R 3 are halogen or C 1 -C 3 alkyl; L1은 C(=W)NR13또는 SO2NR131인 것을 특징으로 하는 페놀 화합물.L 1 is C (= W) NR 13 or SO 2 NR 131 . 3,5-디클로로-4-(3-벤즈아미도프로필옥시)페놀.3,5-dichloro-4- (3-benzamidopropyloxy) phenol. 3,5-디클로로-4-(3-(4-클로로벤즈아미도)프로필옥시)페놀.3,5-dichloro-4- (3- (4-chlorobenzamido) propyloxy) phenol. 3,5-디클로로-4-(3-(4-트리플루오로메틸벤즈아미도)프로필옥시)페놀.3,5-dichloro-4- (3- (4-trifluoromethylbenzamido) propyloxy) phenol. 3,5-디클로로-4-(3-(4-트리플루오로메톡시벤즈아미도)프로필옥시)페놀.3,5-dichloro-4- (3- (4-trifluoromethoxybenzamido) propyloxy) phenol. 3,5-디클로로-4-(4-벤즈아미도부틸옥시)페놀.3,5-dichloro-4- (4-benzamidobutyloxy) phenol. 3,5-디클로로-4-(4-(4-클로로벤즈아미도)부틸옥시)페놀.3,5-dichloro-4- (4- (4-chlorobenzamido) butyloxy) phenol. 3,5-디클로로-4-(4-(4-트리플루오로메틸벤즈아미도)부틸옥시)페놀.3,5-dichloro-4- (4- (4-trifluoromethylbenzamido) butyloxy) phenol. 3,5-디클로로-4-(4-(4-트리플루오로메톡시벤즈아미도)부틸옥시)페놀.3,5-dichloro-4- (4- (4-trifluoromethoxybenzamido) butyloxy) phenol. 3,5-디클로로-4-(3-(5-트리플루오로메틸피콜린아미도)프로필옥시)페놀.3,5-dichloro-4- (3- (5-trifluoromethylpicolinamido) propyloxy) phenol. 3,5-디클로로-4-(4-(5-트리플루오로메틸피콜린아미도)부틸옥시)페놀.3,5-dichloro-4- (4- (5-trifluoromethylpicolinamido) butyloxy) phenol. 3,5-디클로로-4-(3-(4-트리플루오로메틸벤젠술폰아미도)프로필옥시)페놀.3,5-dichloro-4- (3- (4-trifluoromethylbenzenesulfonamido) propyloxy) phenol. 3,5-디클로로-4-(4-(4-트리플루오로메틸벤젠술폰아미도)부틸옥시)페놀.3,5-dichloro-4- (4- (4-trifluoromethylbenzenesulfonamido) butyloxy) phenol. 3,5-디클로로-4-(3-(5-트리플루오로메틸피리딘-2-술폰아미도)프로필옥시)페놀.3,5-dichloro-4- (3- (5-trifluoromethylpyridine-2-sulfonamido) propyloxy) phenol. 3,5-디클로로-4-(4-(5-트리플루오로메틸피리딘-2-술폰아미도)부틸옥시)페놀.3,5-dichloro-4- (4- (5-trifluoromethylpyridine-2-sulfonamido) butyloxy) phenol. 3,5-디클로로-4-(3-(2-푸란카르복사미도)프로필옥시)페놀.3,5-dichloro-4- (3- (2-furancarboxamido) propyloxy) phenol. 3,5-디클로로-4-(4-(2-푸란카르복사미도)부틸옥시)페놀.3,5-dichloro-4- (4- (2-furancarboxamido) butyloxy) phenol. 3,5-디클로로-4-(3-(3-푸란카르복사미도)프로필옥시)페놀.3,5-dichloro-4- (3- (3-furancarboxamido) propyloxy) phenol. 3,5-디클로로-4-(4-(3-푸란카르복사미도)부틸옥시)페놀.3,5-dichloro-4- (4- (3-furancarboxamido) butyloxy) phenol. 3,5-디클로로-4-(3-(5-브로모-2-푸란카르복사미도)프로필옥시)페놀.3,5-dichloro-4- (3- (5-bromo-2-furancarboxamido) propyloxy) phenol. 3,5-디클로로-4-(4-(5-브로모-2-푸란카르복사미도)부틸옥시)페놀.3,5-dichloro-4- (4- (5-bromo-2-furancarboxamido) butyloxy) phenol. 3,5-디클로로-4-(3-(2-티오펜카르복사미도)프로필옥시)페놀.3,5-dichloro-4- (3- (2-thiophenecarboxamido) propyloxy) phenol. 3,5-디클로로-4-(4-(2-티오펜카르복사미도)부틸옥시)페놀.3,5-dichloro-4- (4- (2-thiophenecarboxamido) butyloxy) phenol. 3,5-디클로로-4-(3-(3-티오펜카르복사미도)프로필옥시)페놀.3,5-dichloro-4- (3- (3-thiophenecarboxamido) propyloxy) phenol. 3,5-디클로로-4-(4-(3-티오펜카르복사미도)부틸옥시)페놀.3,5-dichloro-4- (4- (3-thiophenecarboxamido) butyloxy) phenol. 3,5-디클로로-4-(3-(5-메틸-2-티오펜카르복사미도)프로필옥시)페놀.3,5-dichloro-4- (3- (5-methyl-2-thiophenecarboxamido) propyloxy) phenol. 3,5-디클로로-4-(3-(5-메틸-2-티오펜카르복사미도)프로필옥시)페놀.3,5-dichloro-4- (3- (5-methyl-2-thiophenecarboxamido) propyloxy) phenol. 3,5-디클로로-4-(3-(2-피라진카르복사미도)프로필옥시)페놀.3,5-dichloro-4- (3- (2-pyrazinecarboxamido) propyloxy) phenol. 3,5-디클로로-4-(4-(2-피라진카르복사미도)부틸옥시)페놀.3,5-dichloro-4- (4- (2-pyrazinecarboxamido) butyloxy) phenol. 3,5-디클로로-4-(3-(1-메틸-2-인돌카르복사미도)프로필옥시)페놀.3,5-dichloro-4- (3- (1-methyl-2-indolecarboxamido) propyloxy) phenol. 3,5-디클로로-4-(4-(1-메틸-2-인돌카르복사미도)부틸옥시)페놀.3,5-dichloro-4- (4- (1-methyl-2-indolecarboxamido) butyloxy) phenol. 3,5-디클로로-4-(3-(1-메틸-2-피롤카르복사미도)프로필옥시)페놀.3,5-dichloro-4- (3- (1-methyl-2-pyrrolecarboxamido) propyloxy) phenol. 3,5-디클로로-4-(4-(1-메틸-2-피롤카르복사미도)부틸옥시)페놀.3,5-dichloro-4- (4- (1-methyl-2-pyrrolecarboxamido) butyloxy) phenol. 3,5-디클로로-4-(3-(2-퀴놀린카르복사미도)프로필옥시)페놀.3,5-dichloro-4- (3- (2-quinolinecarboxamido) propyloxy) phenol. 3,5-디클로로-4-(4-(2-퀴놀린카르복사미도)부틸옥시)페놀.3,5-dichloro-4- (4- (2-quinolinecarboxamido) butyloxy) phenol. 3,5-디클로로-4-(3-(5-메틸-2-피라진카르복사미도)프로필옥시)페놀.3,5-dichloro-4- (3- (5-methyl-2-pyrazinecarboxamido) propyloxy) phenol. 3,5-디클로로-4-(4-(5-메틸-2-피라진카르복사미도)부틸옥시)페놀.3,5-dichloro-4- (4- (5-methyl-2-pyrazinecarboxamido) butyloxy) phenol. 3,5-디클로로-4-(3-(N-(4-트리플루오로메틸페닐)카르바모일)프로필옥시)-페놀.3,5-dichloro-4- (3- (N- (4-trifluoromethylphenyl) carbamoyl) propyloxy) -phenol. 3,5-디클로로-4-(4-(N-(4-트리플루오로메틸페닐)카르바모일)부틸옥시)페놀.3,5-dichloro-4- (4- (N- (4-trifluoromethylphenyl) carbamoyl) butyloxy) phenol. 3,5-디클로로-4-(3-(N-(5-트리플루오로메틸-2-피디닐)카르바모일)프로필옥시)페놀.3,5-dichloro-4- (3- (N- (5-trifluoromethyl-2-pydinyl) carbamoyl) propyloxy) phenol. 3,5-디클로로-4-(4-(N-(5-트리플루오로메틸-2-피리딜)카르바모일)부틸옥시)페놀.3,5-dichloro-4- (4- (N- (5-trifluoromethyl-2-pyridyl) carbamoyl) butyloxy) phenol.
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